Ethyl cyanoacetate → HCID 178507961, compound

HRID 2050001Notes

Reaction equation

HRID 2050001 reaction equation
[C:1]([CH2:3][C:4](OCC)=[O:5])#[N:2].[NH2:9][C:10]([NH2:12])=[S:11].C[O-].[Na+]>>[NH2:2][C:1]1[CH:3]=[C:4]([OH:5])[N:12]=[C:10]([SH:11])[N:9]=1

Participants

4

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 2723790ThioureaHCID 10942334Sodium Methoxide

Product 1

HCID 178507961HCID 178507961, compound

Procedure

According to a method described by Baker, Joseph, and Schaub, J. Org. Chem. 19, p. 631 (1954) ethyl cyanoacetate is reacted with thiourea in the presence of sodium methoxide to give 4-amino-6-hydroxy-2-mercaptopyrimidine which is methylated in situ to obtain 4-amino-6-hydroxy-2-(methylthio)pyrimidine. Chlorination of the latter compound with phosphorus oxychloride in dimethylaniline gives the desired 4-amino-6-chloro-2-(methylthio)pyrimidine. Yields using this method are uncertain.

Sources & evidence

ORD record
ord-6669e4b77e494334a5082f1624a6b2f0
Source dataset
uspto-grants-1980_04
Patent number
US04199583

Reaction notes

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