Sodium Carbonate → HCID 57825100, compound

Participants

Reaction Conditions

Reaction Steps

A dried pressure tube was charged with (4RS,5RS)-4-(3-bromo-phenyl)-4-(4-methoxy-phenyl)-5-methyl-4,5-dihydro-oxazol-2-ylamine (Building Block AP, (64 mg, 0.2 mmol), pyrimidine-5-boronic acid (25 mg, 0.2 mmol), triphenylphosphine (10 mg, 0.04 mmol), 2 N sodium carbonate solution (0.4 mL), and 1,2-dimethoxyethane (2 mL). The mixture was purged with argon before palladium(II)acetate (4 mg, 0.018 mmol) was added. The sealed pressure tube was heated at 100° C. for 60 hours. The incomplete reaction was stopped, the reaction mixture was cooled and evaporated under reduced pressure. The residue was directly chromatographed on silica gel using a gradient of dichloromethane/methanol=100/0 to 85/15 as the eluent. The mixture of the diastereomeric racemates was chromatographed on a preparative silica gel LC-plate using a 9:1-mixture of dichloromethane/methanol as the eluent. There were obtained 2 fractions of the desired product: 5 mg of a 9:1-mixture of diastereomeric racemates (example 169) [Mass (calculated) C21H20N4O2 [360]; (found) [M+H]+=361 and 3 mg of a 6:4-mixture of diastereomeric racemates (example 170) [Mass (calculated) C21H20N4O2 [360]; (found) [M+H]+=361

Provenance & Evidence