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

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 2.19 g (10.9 mmol) 2-amino-4-chloro-6-methylsulfanyl-pyrimidine-5-carbonitrile in 40 ml benzene at room temperature were added 2,40 g (12.0 mmol) 2-(4-methyl-furan-2-yl)-benzo[1,3,2]dioxaborole, 252mg (0.22 mmol) tetrakis(triphenylphosphine)palladium(O) and 11 ml (22.0 mmol) 2M aqueous sodium carbonate. The reaction mixture was heated at 90° C. for 16 h, then concentrated in vacuo. Chromatography (1/3 ethyl acetate/hexane then 1/1 ethyl acetate/hexane) afforded 1.26 g (47%) 2-amino-4-(4-methyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a light yellow crystalline solid. EI-MS m/e (%): 246 (M+, 61), 245 ([M—H]+, 100).

Provenance & Evidence