Preparation method of 3'-deoxyuridine

A technology of deoxyuridine and lithium hydroxide, applied in the field of preparation of 3'-deoxyuridine, can solve the problems of waste of precious metals, low industrial production feasibility, high risk, etc., and achieves avoiding strict conditions and expensive costs, It is very easy to industrialize large-scale production and avoid the effect of thiocarbonyl reagents

Active Publication Date: 2017-08-11
SHANGHAI ZHAOWEI TECH DEV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first two steps of this route have low selectivity, many by-products, and difficult purification. The third step uses high-pressure H 2 , Pb

Method used

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  • Preparation method of 3'-deoxyuridine
  • Preparation method of 3'-deoxyuridine
  • Preparation method of 3'-deoxyuridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the preparation example of compound 4

[0034]

[0035] Add 50.0g of compound 3 powder, 250mL of acetonitrile and 25mL of acetic anhydride into a 500mL three-neck flask, stir and reflux for 3h, cool to room temperature and filter with suction, wash the solid twice with acetonitrile, and dry the filter cake to obtain 56.3g of compound 4, the yield is 96.0 %.

[0036] 1 H NMR (400MHz, DMSO-d 6 ):δ=10.88(s,1H,N-H),8.42(d,1H,J=7.5Hz,6-H,D 2 O exchange), 7.20 (d, 1H, J = 7.5Hz, 5-H), 5.78 (d, 1H, J = 2.8Hz, 1'-H), 5.49 (d, 1H, J = 4.6Hz, 2' -OH,D 2 O exchange), 5.18 (t, 1H, J = 5.0Hz, 5'-OH, D 2 O exchange), 5.06 (d, 1H, = 5.4Hz, 3'-OH, D 2 O exchange), 4.00-3.88 (m, 3H, 2', 3', 4'-H), 3.77-3.56 (m, 2H, 5', 5"-H), 2.10 (s, 3H, CH 3 C=O). 13 CNMR (101MHz, DMSO-d 6 )δ171.00 (COCH 3 ),162.27(4-C),154.65(2-C),145.35(6-C),95.14(1'-C),90.10(5-C),84.15(4'-C),74.48(2' -C),68.62(3'-C),59.87(5'-C),24.33(CH 3 ).

Embodiment 2

[0037] Embodiment 2: the preparation example of compound 5

[0038]

[0039] Add 50.0 g of compound 4 and 750 mL of acetonitrile into a 2 L three-necked flask, raise the temperature to 65° C., and add a solution of 40 mL of AcBr dissolved in 250 mL of acetonitrile. React at 60-65°C for 1h. Cool to room temperature and spin dry. Dissolved in DCM and washed twice with water, Na 2 SO 4 Dry, spin dry, reflux with 500ml DCM to suspend for 60min, freeze to crystallize after cooling to room temperature, filter with suction, and dry to obtain 57.8g of white crystals of compound 5 with a yield of 76.4%.

[0040] 1 H NMR (400MHz, CDCl 3 )δ=10.25(brs,1H,NHAc),8.14(d,1H,6-H,J=7.6Hz),7.53(d,1H,5-H,J=7.6Hz),5.97(d,1H, 1'-H,J=1..1Hz),5.49(d,1H,2'-H),4.60-4.34(m,4H,3',4',5',5"-H),2.29, 2.17,2.14(3s,9H,3*CH 3 CO). 13 C NMR (101MHz, CDCl 3 )δ171.19, 170.48, 168.98(3*C=O), 163.33(4-C), 154.82(2-C), 144.14(6-C), 96.69(1'-C), 90.80(5-C), 82.54(4'-C),79.67(2'-C),64.81(5'-C),48.83(3'-C...

Embodiment 3

[0041] Embodiment 3: the preparation example of compound 6

[0042]

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Abstract

The invention relates to the field of pharmaceutical synthesis and particularly relates to a preparation method of 3'-deoxyuridine. The method comprises the steps: by adopting a compound 3 as a raw material, firstly protecting amino through acetic anhydride to obtain a compound 4, obtaining a compound 5 under the action of acetyl bromide, reducing through a hypophosphite system to obtain a compound 6; removing deacetylated amino under the action of high-pressure water vapor and an organic solvent to obtain a compound 8 or removing N-acetyl to obtain a compound 7; and finally removing all acetyl to obtain a mixture of 3'-deoxyuridine and 3'-deoxycytidine; separating and purifying to obtain 3'-deoxyuridine crystal and 3'-deoxycytidine crystal separately, or directly removing all acetyl through the compound 6 to obtain the 3'-deoxycytidine. Available natural products are taken as initial raw materials, so that the method is simple in operation and convenient to purify, and industrial large-scale production is extremely easy to implement.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a preparation method of 3'-deoxyuridine. Background technique [0002] Nucleic acid is a very important genetic material in organisms. There are two types of nucleic acids in nature, DNA and RNA. They are composed of nucleotide basic units, and the nucleotides are connected by 3'-5'-phosphodiester bonds. [0003] Although people simply thought that nucleic acid was the genetic molecule in the organism at first, from the perspective of modern biochemical information flow, the biochemical information in the organism is transmitted from DNA to RNA, and finally to protein, so it can be seen that nucleic acid molecules are It plays a more diverse and complex role in biological cells. In simple terms, a DNA sequence representing a specific gene is transcribed in the nucleus into a heterogeneous RNA in the nucleus, which is further transcribed to obtain a mature RNA, and then the mature R...

Claims

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Application Information

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IPC IPC(8): C07H19/06C07H1/00C07H1/06
CPCC07H1/00C07H1/06C07H19/06
Inventor 王利民于高辉姚峰熊晶晶田禾韩建伟
Owner SHANGHAI ZHAOWEI TECH DEV
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