Dimethylformamide → HCID 86719402, compound

Participants

Reaction Conditions

Reaction Steps

At −78° C. under N2 atmosphere, to a solution of (R)-tert-butyl 3-(6-bromo-4-(tert-butoxycarbonylamino)-5-(4-phen-oxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate (119) (1.57 g, 2.41 mmol) in THF (20 mL) was added n-BuLi (3 mL, 7.23 mmol, 2.5M in THF) dropwise. The resulting mixture was stirred at −78° C. for 1 hr before introducing DMF (264 mg, 3.62 mmol). Stirring was continued for another 1 hr at −78° C. The reaction was quenched with sat. NH4Cl before extracted with EA (30 mL×3). Combined organic layers were washed with brine and dried over Na2SO4. Solvents were removed under vacuum and the residue was purified by flash chromatography (silica gel, 0 to 50% EA in PE) to provide (R)-tert-butyl 3-(4-(tert-butoxycarbonylamino)-6-formyl-5-(4-phenoxyphenyl)-7H-pyrr-olo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate (120) (118 mg, 8%) as a yellow oil. LC-MS (ESI): m/z (M+1) 600.0.

Provenance & Evidence