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Method for preparation of 2-ethyl-4-amtno-5-cyanopyrimidine

A technology of cyanopyrimidine and amino, which is applied in the field of preparation of 2-methyl-4-amino-5-cyanopyrimidine, and achieves the effects of high yield, short process route and convenient industrial production

Inactive Publication Date: 2013-08-21
DSM IP ASSETS BV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method still cannot avoid the harsh conditions of the oxidative dehydrogenation reaction of expensive N,N-dimethylformamide diethyl acetal and dimethylaminopropionitrile

Method used

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  • Method for preparation of 2-ethyl-4-amtno-5-cyanopyrimidine
  • Method for preparation of 2-ethyl-4-amtno-5-cyanopyrimidine
  • Method for preparation of 2-ethyl-4-amtno-5-cyanopyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Put cyanoacetamide (50g, 0.6mol), N,N-dimethylformamide (91g, 1.25mol) and pyridine (4.7g, 0.06mol) in a dry reaction flask, cool down to -10°C, and Phosphorus oxychloride (193 g, 1.25 mol) was added dropwise within 3 hours, and the mixture was stirred at -10°C for 12 hours after the drop was completed. After the reaction was completed, the mixture was poured into ice water (700mL), adjusted to pH=3, extracted with dichloromethane (300ml×3), the extracts were combined and concentrated to give orange oil (II) (R 1 =R 2 =CH 3 , 54g, 74%), the purity is 98% (GC).

[0029] Cool the methanol solution (400mL) of sodium methoxide (26.5g, 0.49mol) to 0°C, add acetamidine hydrochloride (46.3g, 0.49mol) in batches, stir at 0°C for 20min, filter, and pour the filtrate into the above oil Stir at 25°C for 12h, filter, wash with methanol (3×20mL), and dry in vacuo (50°C, 2h, -0.1MPa) to obtain 51.8g of white solid, yield 65% (calculated as cyanoacetamide), Purity 99% (GC).

[00...

Embodiment 2

[0033] Put cyanoacetamide (50g, 0.6mol), N,N-dimethylacetamide (126.4g, 1.25mol), pyridine (4.7g, 0.06mol) in a dry reaction flask, cool down to -10°C, Phosphorus oxychloride (193 g, 1.25 mol) was added dropwise within 3 h, and the mixture was stirred at -10°C for 12 h after the drop was completed. After the reaction was completed, the mixture was poured into ice water (700mL), adjusted to pH=3, extracted with dichloromethane (300ml×3), the extracts were combined and concentrated to give orange oil (II) (R 1 =R 2 =C 2 h 5 , 64.4g, 72%) with a purity of 98% (GC).

[0034]Cool the methanol solution (400mL) of sodium methoxide (25.4g, 0.47mol) to 0°C, add acetamidine hydrochloride (44.4g, 0.47mol) in batches, after the addition is complete, stir at 0°C for 20min, filter, and pour the filtrate into the above In the oil, stirred at 25°C for 12h, filtered, washed with methanol (3×20mL), and dried in vacuum (50°C, 2h, -0.1MPa) to obtain 50.2g of white solid, yield 63% (calculated...

Embodiment 3

[0036] Put cyanoacetamide (50g, 0.6mol), N,N-dimethylformamide (91g, 1.25mol) and pyridine (4.7g, 0.06mol) in a dry reaction flask, cool down to -5°C, and Phosphorus oxychloride (193 g, 1.25 mol) was added dropwise within 3 hours, and the mixture was stirred at -5°C for 12 hours after the drop was completed. After the reaction was completed, the mixture was poured into ice water (700mL), adjusted to pH=3, extracted with dichloromethane (300ml×3), the extracts were combined and concentrated to give orange oil (II) (R 1 =R 2 =CH 3 , 49g, 68%), the purity is 98% (GC).

[0037] Cool the methanol solution (400mL) of sodium methoxide (24.4g, 0.45mol) to 0°C, add acetamidine hydrochloride (42.5g, 0.45mol) in batches, stir at 0°C for 20min, filter, pour the filtrate into the above oil Stir at 25°C for 12h, filter, wash with methanol (3×20mL), and dry in vacuo (50°C, 2h, -0.1MPa) to obtain 48.2g of white solid, yield 60% (calculated as cyanoacetamide), Purity 99% (GC). 1 H-NMR and...

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PUM

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Abstract

Disclosed is a method for preparation of 2-methyl-4-amino-5-cyanopyrimidine (I). The present method comprises the steps of reacting cyanoacetamide with formamide derivatives in the presence of various acyl halides and catalysts to produce compound (II), and condensing the compound (II) with acetamide hydrochloride in the present of a base to obtain 2-methyl-4-amino-5-cyanopyrimidine (I).

Description

Technical field: [0001] The invention belongs to the field of organic chemistry and relates to a preparation method of 2-methyl-4-amino-5-cyanopyrimidine (I). [0002] Background technique [0003] 2-Methyl-4-amino-5-cyanopyrimidine (I) is an important intermediate in the synthesis of vitamin B1 (Vitamin B1). [0004] French Patent 819596, Norwegian Patent 59015 and Swiss Patent 193951, 193952, German Patent 671787 describe the preparation of ethoxymethylene malonate (IV) as starting material with malonate, then condense with acetamidine, and then Chlorination, ammoniation and dehydration in the system (I). The method has a lengthy route and a low yield (the one-step condensation of compound (IV) and acetamidine only has a 60% yield), and has no practical value. [0005] [0006] Todd A et al. (J.Chem.Soc., 1937,1364) improved the above-mentioned method, using cyanoacetate as starting material to prepare ethoxymethylene cyanoacetate (Ⅴ), compound (Ⅴ) and After conde...

Claims

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Application Information

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IPC IPC(8): C07D239/42
CPCC07D239/42
Inventor 陈芬儿赵磊熊方均
Owner DSM IP ASSETS BV
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