Acetic Acid → HCID 68734971, compound

Participants

Reaction Steps

To a suspension of 4-{5-[2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyridin-3-yl}-benzaldehyde (Intermediate 58) (1 eq, 0.243 mmol, 100 mg) and methylamine hydrochloride (Sigma-Aldrich, St. Louis, USA) (1 eq, 0.243 mmol, 16.7 mg) in DCM (1 ml) is added AcOH (1.1 eq, 0.267 mmol, 15.3 ul). The solution is stirred for 5 min, then NaBH(OAc)3 (1.05 eq, 0.255 mmol, 57 mg) is added. After stirring the resulting mixture at r.t. for 1.5 h the solvents are removed in vacuo. The residue is taken up in aqueous NaHCO3 solution and extracted with DCM. The organic layer is washed with brine, dried over MgSO4, and filtered. The solvents are removed in vacuo and purification of the residue by reversed phase HPLC is yielding the title compound; [M+H]+=407; 1H-NMR (400 MHz, CDCl3): δ 12.52 (s, 1H), 9.43 (s, 1H), 8.95 (s, 1H), 8.73 (s, 1H), 8.66 (d, 1H), 7.83 (t, 1H), 7.64 (d, 2H), 7.49-7.46 (m, 3H), 7.32 (d, 1H), 6.88 (d, 1H), 3.86 (s, 2H), 2.75 (s, 3H), 2.56 (s, 3H).

Provenance & Evidence