Potassium Carbonate → HCID 11704577, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-5-(1,3-thiazol-2-yl)thieno[2,3-d]pyrimidine (0.050 g, 0.20 mmol), 5-(3-aminopropoxy)-N-methylpyridine-2-carboxamide trifluoroacetate (0.070 g, 0.22 mmol), potassium carbonate (0.272 g, 1.97 mmol) and N,N-dimethylacetamide (2.4 mL) was heated at 120° C. for 13 h. The solvent was evaporated in vacuo, and the residue was treated with 5% sodium bicarbonate (20 mL) and ethyl acetate (20 mL). The precipitate was filtered and washed with water and ethyl ether. The resulting white solid was purified by column chromatography over silica gel to give 70 mg (81%) N-methyl-5-(3-[5-(1,3-thiazol-2-yl)thieno[2,3-d]pyrimidin-4-yl]aminopropoxy)pyridine-2-carboxamide. MS [M+H]=427, LC/MS (EI) tR 3.54 min (Method D), 1H NMR (10% MeOD/CDCl3) δ (ppm) 10.85 (s, 1H), 8.30 (s, 1H), 8.12 (d, J=2.4 Hz, 1H), 8.00 (d, J=8.7 Hz, 1H), 7.94 (b, 1H), 7.71 (s, 1H), 7.50 (d, J=3.6 Hz, 1H), 7.28 (s, 1H), 7.21 (dd, J=8.7, 3.0 Hz, 1H), 4.15 (t, J=0.6 Hz, 2H), 3.80-3.74 (m, 2H), 2.94 (d, J=0.6 Hz, 3H), 2.24-2.18 (m, 2H).

Provenance & Evidence