Methyl iodide → Malononitrile

HRID 895043Notes

Reaction equation

HRID 895043 reaction equation
CI.[NH2:3][C:4]1[CH:9]=[C:8](N)[NH:7][C:6](=[S:11])[N:5]=1>[OH-].[Na+]>[NH2:5][C:6]([NH2:7])=[S:11].[C:8](#[N:7])[CH2:9][C:4]#[N:3]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 12014824,6-Diamino-2(1H)-pyrimidinethione

Product 2

HCID 8010MalononitrileHCID 2723790Thiourea

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methyl iodide (169.0 g., 1.19 mole) is added in one portion to a stirred solution of 4,6-diaminopyrimidine-2(1H)thione (146 g., 1.02 mole) in 1.0 liter 1N sodium hydroxide. The thione starting material is obtained by reaction of thiourea and malononitrile according to Kikugawa, et al., Chem. Pharm. Bull., 25(7), 1811-1821 (1977). In about five minutes following the addition a precipitate forms. After stirring overnight, the reaction mixture is filtered and air-dried affording 135.1 g. (81%) of 4,6-diamino-2-(methylthio)pyrmidine; m.p. 185°-186° (recrystallized from acetonitrile).

Sources & evidence

ORD record
ord-5322519bb9e24e9b98d7a663cfeec0d4
Source dataset
uspto-grants-1981_08
Patent number
US04286093

Reaction notes

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