Benzhydrylamine → N-benzhydryl-2-(benzyloxymethyl)-4-hydroxypyrimidine-5-carboxamide

Participants

Reaction Steps

A mixture of step D product (2-e) (20.0 g, 76.9 mmol), diphenylmethanamine (15.5 g, 84.6 mmol), HATU (43.8 g, 115.0 mmol), and TEA (23.3 g, 230 mmol) in DMF (100 mL) were combined and stirred at the ambient temperature overnight. Ice-water (40 mL) was added to the reaction mixture and extracted with DCM (30 mL×2). The organic phase was concentrated to give a residue, which was purified by silica gel chromatography (eluented with PE/EA=3:1˜1:1) to a afford the product, 2-f, (31.0 g, 96%). 1H NMR (300 MHz, CD3OD): δ4.29 (s, 2H), 4.52 (s, 2H), 6.22 (s, 1H), 7.21-7.23 (m, 15H), 8.60 (s, 1H). LC-MS: (M+H)+ 426.

Provenance & Evidence