Methylamine → HCID 69220139, compound
Reaction equation
[C:1]([C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([CH3:17])[CH:11]=2)[C:6]([C:18]2[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=2)=[N:5][C:4]=1SC)#[N:2].[CH3:28][NH2:29]>C(O)C>[C:1]([C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([CH3:17])[CH:11]=2)[C:6]([C:18]2[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=2)=[N:5][C:4]=1[NH:29][CH3:28])#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A suspension of 5-cyano-1-(3,4-dimethylphenyl)-4-(methylthio)-2-[4-(methylthio)phenyl]-6-oxo-1,6-dihydropyrimidine (1 g, 2.5 mmol) (prepared according to example 10) in ethanol (10 ml) with methylamine (0.16 g, 5 mmol) was refluxed for 3 hr. Then the reaction mass poured on to ice and the resulted solid filtered, washed thoroughly with water. The solid thus obtained was purified by column chromatography using ethyl acetate and hexane mixture as eluent to yield title compound (0.36 g, yield 38%, mp 199-205° C., purity 98.72% by HPLC). 1H-NMR (CDCl3):δ 2.19 (s, 3H), 2.22 (s, 3H), 2.44 (s, 3H), 3.17-3.18 (d, 3H), 5.73 (s, 1H, D2O exchangeable) 6.75-6.77 (d, 2H), 6.90 (s, 1H), 7.02-7.06 (m, 3H), 7.24-7.26 (d, 1H). IR (KBr) cm−1: 3280, 2920, 2207 (—CN), 1661 (—C═O). MS m/z:377.2 (M+).