Methyl iodide → HCID 178503559, compound

HRID 2050002Notes

Reaction equation

HRID 2050002 reaction equation
[NH:1]1[C:8](=[O:9])[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].[CH3:10]OS(OC)(=O)=O.CI>>[OH:9][C:8]1[CH:7]=[C:5]([OH:6])[N:4]=[C:2]([S:3][CH3:10])[N:1]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 6497Dimethyl SulfateHCID 2723628Thiobarbituric acid

Product 1

HCID 178503559HCID 178503559, compound

Procedure

Another method described by Wheeler and Jamieson, Am. Chem. J. 32, p. 345 (1904) initiates the synthesis with 2-thiobarbituric acid which is methylated. Either dimethylsulfate or methyl iodide is used to obtain 4,6-dihydroxy-2-methylthiopyrimidine. Dichlorination at 4- and 6- positions is accomplished with phosphorus oxychloride in the presence of dimethylaniline, and the 4,6-dichloro-2-(methylthio)pyrimidine thus obtained is reacted with aqueous alcoholic ammonia to produce the desired 4-amino-6-chloro-2-(methylthio)pyrimidine.

Sources & evidence

ORD record
ord-1a7f62f0a6b54981a61ec90b725f4eb4
Source dataset
uspto-grants-1980_04
Patent number
US04199583

Reaction notes

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