Sodium Hydroxide → HCID 68637190, compound

Participants

Reaction Steps

Sodium triacetoxyborohydride (0.23 g, 1.1 mmol) was added to a mixture of N-(3-fluorophenyl)-2-(4-{[7-(pyrrolidin-3-ylmethoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)acetamide bis(trifluoroacetate) (0.30 g, 0.44 mmol) and (tert-butyldimethylsilyloxy)acetaldehyde (0.20 ml, 1.0 mmol) in tetrahydrofuran (9 ml) and methanol (3 ml) containing a catalytic amount of acetic acid. The mixture was stirred at room temperature for 1 hour. The mixture was poured into sodium hydroxide solution (1M) and extracted with dichloromethane. The organic layer was separated, washed with brine, dried over magnesium sulphate and then evaporated to leave a brown oil which was purified by silica gel chromatography. Elution with 3 to 6% methanol in dichloromethane gave 2-{4-[(7-{[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyrrolidin-3-yl]methoxy}quinazolin-4-yl)amino]-1H-pyrazol-1-yl}-N-(3-fluorophenyl)acetamide. MS (+ve ESI): 620 (M+H)+.

Provenance & Evidence