Hydrochloric Acid → HCID 10178676, compound

Participants

Reaction Steps

Sodium borohydride (9 mg, 0.24 mmol) was added in one portion to a suspension of 2-(4-benzoylanilino)-4-(imidazo-[1,2-a]-pyridin-3-yl)-pyrimidine (27 mg, 0.069 mmol) in methanol (2 mL). The mixture was stirred at room temperature for 63 hours. HCl (5 mL, 1 M) was added and the mixture was stirred for another 15 min. After evaporation of the solvent in vacuo, the residue was suspended in water and extracted with chloroform. The phases were separated and the organic phase was dried (MgSO4) and the solvent was evaporated in vacuo. The crude material was purified on a silica gel column using chloroform/EtOH, 95:5, as the eluent to give 24 mg (88% yield) of the product as a pale yellow solid: mp 213-216° C.; MS (TSP) m/z 394 (M+1), 1H NMR (400 MHz, DMSO-d6) δ 9.87 (d, J=5.9 Hz, 1 H), 9.43 (s, 1 H), 8.43 (s, 1 H), 8.23 (d, J=5.48 Hz, 1 H), 7.58 (d, J=9.0 Hz, 1 H), 7.46 (d, J=8.4 Hz, 2 H), 7.29 (m, 1 H), 7.23 (m, 2 H), 7.20 (d, J=5.5 Hz, 1 H), 7.14 (m, 4 H), 7.04 (m, 1 H), 6.88 (m, 1 H), 5.51 (s, 1 H).

Provenance & Evidence