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Dihydro pyrimidone sulfoacid as well as salt compound and preparation method thereof

A technology of dihydropyrimidinone sulfonate and dihydropyrimidinone sulfonic acid is applied in the field of synthesizing heterocyclic compounds, and can solve the problem of low water solubility, influence on drug availability and effective time, dihydropyrimidinone/thione class Problems such as low water solubility and fat solubility of compounds

Inactive Publication Date: 2010-07-21
GANNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0004] However, dihydropyrimidinone / thione compounds have low water solubility and fat solubility. In terms of medicine, they can only be made into oral preparations and cannot be made into injections. In addition, their low water solubility affects their medicines. Utilization and effective time
The sulfonation modification of dihydropyrimidinone compounds has not been reported in the literature, and sulfonic acid and its salts have greater water solubility and higher medicinal value

Method used

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  • Dihydro pyrimidone sulfoacid as well as salt compound and preparation method thereof
  • Dihydro pyrimidone sulfoacid as well as salt compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 5-ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one (2.6 g, 10.0 mmol), 20 mL of dichloromethane to the dry reactor, Cool in an ice-salt bath, stir and add chlorosulfonic acid (2.0mL, 30.0mmol), heat up to 40°C after addition, stir, react for 30 minutes, cool, stand still, separate the upper layer of dichloromethane, wash the lower layer with acetonitrile, and precipitate The white precipitate was filtered and recrystallized with ethanol-water to obtain 5-ethoxycarbonyl-2-oxo-4-phenyl-3,4-dihydropyrimidin-2(1H)-one-6-methylsulfonic acid, the product 2.7 g, 79% yield, m.p. 274°C (decomp.).

[0020] Molecular formula is C 14 h 16 N 2 o 6 S, ESI-MS m / z (%): 339.35 (M - , 100). Anal. Calc.: C, 49.40; H, 4.74; N, 8.23; S, 9.42%; found: C, 49.24; H, 4.68; N, 8.15;

[0021] IR (KBr, cm -1 ): v3244, 3105, 2982, 1699, 1644, 1456, 1229, 1171, 1096.

[0022] 1 H NMR (400MHz, D 2 O): δ1.08(t, 3H, J=7.0Hz, CH 3 ), 4.00 (q, 2H, J=7.0Hz, CH 3 -Et), 4.43(q...

Embodiment 2

[0024] To the dry reactor was added 5-ethoxycarbonyl-4-(4'-chlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one (2.9 g, 10.0 mmol) , 20mL of dichloromethane, cooled in an ice-salt bath, stirred and added dropwise chlorosulfonic acid (2.0mL, 30.0mmol), heated to 40°C after the addition, stirred, reacted for 30 minutes, cooled, stood still, separated the upper layer of dichloromethane, and the lower layer The substance was washed with acetonitrile, and a white precipitate was precipitated, filtered, eluted with a mixture of ethyl acetate and methanol (2:1), and column chromatography gave 5-ethoxycarbonyl-2-oxo-4-(4'-chlorophenyl )-3,4-dihydropyrimidin-2(1H)-one-6-methanesulfonic acid product 2.5g, yield 67%, m.p.210°C.

[0025] Molecular formula is C 14 h 15 ClN 2 o 6 S, ESI-MS m / z (%): 373.16 (M - , 100).Anal.Calc.: C, 44.86; H, 4.03; Cl, ​​9.46; N, 7.47; S, 8.56%; found: C, 44.62; 8.43%.

[0026] IR (KBr, cm -1 ): v3273, 3011, 2939, 1710, 1659, 1232, 1181, 1127, 1042....

Embodiment 3

[0030] Add 5-ethoxycarbonyl-4-methyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one (1.98g, 10mmol) to the dry reactor, 20mL dichloromethane, ice Cool in a salt bath, stir and add chlorosulfonic acid (2.0mL, 30mmol) dropwise, heat up to 40°C after addition, stir, react for 30 minutes, cool, let stand, separate the upper layer of dichloromethane, wash the lower layer with ether, and precipitate white The solid was filtered by suction, eluted with a mixture of ethyl acetate and methanol (2:1), and column chromatography gave 5-ethoxycarbonyl-2-oxo-4-methyl-3,4-dihydropyrimidine-2 ( 1H)-Keto-6-methylsulfonic acid product 2.5g, yield 90%, m.p.207°C.

[0031] Molecular formula is C 9 h 14 N 2 o 6 S, ESI-MS m / z (%): 277.34 (M - , 100). Anal. Calc.: C, 38.84; H, 5.07; N, 10.07; S, 11.52%; found: C, 38.75;

[0032] IR (KBr, cm -1 ): v3298, 3025, 2936, 1716, 1575, 1233, 1167, 1139, 1031.

[0033] 1 H NMR (400MHz, D 2 O): δ1.15(d, 3H, J=6.40Hz, CH 3 -Pyr), 1.19(t, 3H, J=6.95Hz, CH 3...

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Abstract

The invention relates to a six-membered heterocyclic pyrimidone compound containing two nitrogen atoms, belonging to the technical field of heterocyclic compounds. The invention also provides a method for sulfonating and deriving 6-site carbon substituting alkyl of a mother nucleus dihydro pyrimidone compound and obtains a novel dihydro pyrimidone sulfoacid and a salt compound thereof. The preparation method has simple process and high yield and mainly comprises the following steps of: adding a dihydro pyrimidone compound and a sulfonating agent to a dispersing agent for sulfonation reaction; then carrying out conventional separation and purification to obtain a dihydro pyrimidone sulfoacid compound; and reacting the dihydro pyrimidone sulfoacid compound with alkali and a metallic oxide or salt to obtain the corresponding dihydro pyrimidone sulphosalts compound. The novel compound comprises the dihydro pyrimidone sulfoacid and the salt compound thereof, improves the water solubility of a mother nucleus compound, i.e. the dihydro pyrimidone compound, and prepares the mother nucleus compound into medicaments, thereby enhancing the availability of the medicaments and shortening the effective time; in addition, the novel compound has favorable medicinal values.

Description

1. Technical field [0001] The present invention relates to the synthesis of a class of heterocyclic compounds containing two nitrogen atoms, specifically the invention of 5-(alkyl or alkoxy) carbonyl-6-alkyl-4-(aryl or alkyl)-3 , sulfonic acid derivatives of 4-dihydropyrimidin-2(1H)-one compounds and their salt compounds and the preparation method of these novel compounds. The invention replaces the α carbon (sp 3 A sulfonic acid group has been introduced on the hybrid carbon), and a class of novel compounds-dihydropyrimidinone sulfonic acid compounds have been obtained, which can be reacted with alkalis, metal oxides or salts to obtain corresponding dihydropyrimidinone sulfonates compound. The sulfonation reaction of the present invention can efficiently realize sp by one-step reaction 3 The cleavage of the hybrid carbon C-H bond and the formation of the C-S bond have obtained a new class of compounds-dihydropyrimidinone sulfonic acid and its salts in high yield. These com...

Claims

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Application Information

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IPC IPC(8): C07D239/22
Inventor 谢永荣杜恣毅樊晓辉周中高谢步云卢莹冰
Owner GANNAN NORMAL UNIV
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