Hydrochloric Acid → 4-Amino-2-chloro-6-(methylthio)pyrimidine-5-carbonitrile

HRID 1586952Notes

Reaction equation

HRID 1586952 reaction equation
COC(SC)=C(C#N)C#N.N#CN.[C:14]([C:16](=[C:19]([NH:22][C:23]#[N:24])[S:20][CH3:21])[C:17]#[N:18])#[N:15].[ClH:25]>>[NH2:15][C:14]1[C:16]([C:17]#[N:18])=[C:19]([S:20][CH3:21])[N:22]=[C:23]([Cl:25])[N:24]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 14150559Dicyanoketene Dimethyl ThioacetalHCID 187532732,2-Dicyano-1-methylsulfanyl-vinyl-cyanamide

Product 1

HCID 118304584-Amino-2-chloro-6-(methylthio)pyrimidine-5-carbonitrile

Procedure

Process for the production of 4-amino-2-chloro-5-cyano-6-(methylthio)pyrimidine of the formula: ##STR9## comprising reacting malononitrile with carbon disulfide in the presence of a strong base to obtain a dianion of dicyanodithioacetic acid of the formula: ##STR10## and then is methylating the dianion of dicyanodithioacetic acid of formula II with a methylating agent to obtain a dicyanoketene dimethyl thioacetal of the formula: ##STR11## condensing the dicyanoketene dimethyl thioacetal of formula III with cyanamide in the presence of a base to obtain an anion of 2-cyano-3-cyanamino-3-methylthio-acrylonitirile of the formula: ##STR12## and then the anion of 2-cyano-3-cyanoamino-3-methylthio-acrylonitrile of formula IV is cyclized in the presence of hydrochloric acid to obtain the 4-amino-2-chloro-5-cyano-6-(methylthio)pyrimidine.

Workup

  1. customto obtain an anion of 2-cyano-3-cyanamino-3-methylthio-acrylonitirile of the formula

Sources & evidence

ORD record
ord-8c7e9fbaf2a645588c0c88e858fe6f40
Source dataset
uspto-grants-1993_06
Patent number
US05216160

Reaction notes

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