Diisopropylethylamine → HCID 178457488, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(3-phenyl-pyridin-2-ylmethyl)-pyrimidine-4-carboxylic acid (164) (370 mg, 0.89 mmol) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropyl-amine (8b) (292 mg, 1.34 mmol) in dimethylformamide (5 mL) was added N,N-diisopropylethylamine (0.5 mL, 2.69 mmol), the mixture was cooled to 0° C., T3P (50 wt % in ethyl acetate) (1.8 g, 2.69 mmol) was added, and the mixture was stirred for 16 h at room temperature. Silica thin layer chromatography was performed (5% methanol in dichloromethane, Rf=0.3). Water (100 mL) was added, the mixture was extracted with ethyl acetate, dried and concentrated, and purified by a CombiFlash column (eluted at 2-5% methanol in dichloromethane) to get 5-benzyloxy-6-hydroxy-2-(3-phenyl-pyridin-2-ylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (165) (200 mg, 36.46%) as a yellow sticky product.

Provenance & Evidence