Potassium tert-butoxide → HCID 56971109, compound

Participants

Reaction Steps

A mixture of 3-(dimethylamino)-1-(2-methyl-3-f uranyl)-2-(2-methyl-4-pyridinyl)-2-propen-1-one (541 mg, 2.000 mmol) and 3-methyl-1-piperidinecarboximidamide hydrochloride (533 mg, 3 mmol) in ethanol (10 ml) was stirred at room temperature. Potassium tert-butoxide (449 mg, 4.00 mmol) was added and the mixture was heated at reflux for 90 minutes. After cooling to room temperature the solvent was evaporated and the residue 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 in isohexane to give 4-(2-methyl-3-furanyl)-2-(3-methyl-1-piperidinyl)-5-(2-methyl-4-pyridinyl)pyrimidine as a gum (460 mg, 66%). A solution of 4-(2-methyl-3-furanyl)-2-(3-methyl-1-piperidinyl)-5-(2-methyl-4-pyridinyl)pyrimidine (460 mg, 1.3 mmol) in dichloromethane (2 ml) was treated with hydrogen chloride (1M in diethyl ether, 1.5 ml). The solvent was evaporated and the residue was co-evaporated with diethyl ether (×2). The residue was triturated with diethyl ether and the resulting solid was collected, washed with diethyl ether and dried to give the title compound as a pale yellow solid (450 mg, 89%). LC/MS [M+H]+=349. 1H NMR (400 MHz, d6-DMSO): δ 8.59 (1H, d), 8.54 (1H, s), 7.81 (1H, s), 7.57-7.52 (1H, m), 7.51 (1H, d), 6.02 (1H, d), 4.70-4.60 (2H, m), 3.06-2.98 (1H, m), 2.70-2.77 (1H, m), 2.66 (3H, s), 2.39 (3H, s), 1.84-1.19 (5H, m), 0.93 (3H, d).

Provenance & Evidence