Sodium hydride → 2-Amino-4-(3-methyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

6.32 g (39.5 mmol) guanidine carbonate was added portionwise to a stirred suspension of 0.7 g (17.5 mmol, 60% dispersion in mineral oil) sodium hydride in 70 ml DMF under argon at room temperature and stirring continued at 40° C. for 30 minutes. A solution of 7.4 g (29.2 mmol) 2-(3-methyl-furan-2-carbonyl)-3,3-bis-methylsulfanyl-acrylonitrile in 15 ml DMF was then added dropwise and the reaction mixture heated at 100° C. for 30 minutes. The reaction mixture was then poured onto 2 l ice-water, and the precipitate collected by filtration and dried in vacuo to afford 6.12 g (85%) 2-amino-4-(3-methyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a yellow solid. ES-MS m/e (%): 247 (M+H+, 100).

Provenance & Evidence