Formaldehyde → HCID 68906214, compound

Participants

Reaction Steps

To 2-{5-bromo-2-[2-(4-methylpiperidin-4-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid cyclopropylamide dihydrochloric acid (0.200 g, 0.34 mmol) dissolved in 3:1 MeOH:dichloromethane (8 mL) is added 37.4% aqueous formaldehyde (0.076 mL, 1.02 mmol). After 1 hour, the reaction mixture is cooled in an ice bath and sodium borohydride is added in portions over two minutes. The reaction proceeds for 1 hour in an ice bath and 1 hour at room temperature. By TLC an intermediate is present and an additional equivalent of sodium borohydride is added at 0° C. After 30 minutes the entire reaction mixture is loaded onto a silica gel column and chromatographed, eluting with 3-7% (2 M NH3 in MeOH) in dichloromethane to give 116 mg, 64% yield, of the methylated product. It is converted to the titled compound by treating with concentrated HCl solution and isolated as a yellow solid. ES+(m/z) 528 (79Br) and 530 (81Br) [M(free base)+H].

Provenance & Evidence