Sodium hydride → 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a slurry of NaH (1.68 g, 42.1 mmol, 60% in oil) in 300 mL of DMF at RT, was added 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (10 g, 38.3 mmol) via a solid addition funnel over 45 min. After addition of the amine was complete, 4-fluorobenzaldehyde (5.0 g, 40.2 mmol) was added dropwise to the reaction mixture. The reaction was heated to 100° C. for 24 hr, an additional NaH (0.25 equivalents) was added and the mixture stirred at 100° C. for another 24 hr. The reaction was cooled to RT for 2 hr, a precipitate formed upon cooling. The reaction mixture was filtered, washed sequentially with water, then Et2O to afford a tan solid, 6.5 g, 47% yield.

Provenance & Evidence