Diisopropylethylamine → HCID 178484774, compound

Participants

Reaction Steps

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (404) (250 mg, 0.56 mmol) in dimethylformamide (5 mL) was added N,N-diisopropylethylamine (0.3 mL, 1.69 mmol) followed by [2-(tert-butyl-dimethylsilanyloxy)-ethyl]methyl-amine (8a) (320 mg, 1.69 mmol) and HATU (320 mg, 0.84 mmol) and stirring was continued for 1 h (TLC, ethyl acetate, Rf=0.5). Water (30 mL) was added and the mixture was extracted with ethyl acetate (2×20 mL). The organic part was washed with water (2×100 mL) and brine (2×50 mL). The organic phase was thereafter dried and concentrated. The crude product was purified by Combi-Flash column (eluted at 30-40% ethyl acetate in hexane) to get 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amide (405) (300 mg, 87%) as a light yellow sticky solid.

Provenance & Evidence