Potassium tert-butoxide → HCID 56971108, compound

Participants

Reaction Steps

A mixture of 3-(dimethylamino)-1-(2-methyl-3-furanyl)-2-(3-pyridinyl)-2-propen-1-one (256 mg, 1 mmol) and 3-methyl-1-piperidinecarboximidamide hydrochloride (267 mg, 1.5 mmol) in ethanol (5 ml) was stirred at room temperature. Potassium tert-butoxide (224 mg, 2 mmol) was added and the mixture was heated at reflux for 45 minutes. After cooling to room temperature the reaction mixture was diluted with water and extracted with ethyl acetate. The organic extracts were combined, washed with water and brine, dried and evaporated. The residue was purified by silica gel chromatography eluting with 25% ethyl acetate and isohexane to give 4-(2-methyl-3-furanyl)-2-(3-methyl-1-piperidinyl)-5-(3-pyridinyl)pyrimidine (28 mg, 8%). A solution of 4-(2-methyl-3-furanyl)-2-(3-methyl-1-piperidinyl)-5-(3-pyridinyl)pyrimidine (28 mg, 0.084 mmol) in dichloromethane (1 ml) was treated with hydrogen chloride (1M in diethyl ether, 0.1 ml). The solvent was evaporated and the residue co-evaporated with dichloromethane (×2). The resulting solid was dried to give the title compound as a solid (24 mg, 77%). LC/MS [M+H]+=335. 1H NMR (400 MHz, d6-DMSO): δ 8.75-8.73 (2H, m), 8.45 (1H, s), 8.17 (1H, d), 7.86-7.82 (1H, m), 7.45 (1H, d), 5.87 (1H, d), 4.65-4.59 (2H, m), 3.02-2.95 (1H, m), 2.71-2.65 (1H, m), 2.38 (3H, s), 1.91-1.18 (5H, m), 0.92 (3H, d).

Provenance & Evidence