Sodium Carbonate → N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-(2-thienyl)pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (170 mg, 0.64 mmol, 1.0 equiv.), thiophen-2-ylboronic acid (107 mg, 0.83 mmol, 1.3 equiv.), Pd(PPh3)4 (148 mg, 0.128 mmol, 0.2 equiv.), Na2CO3 (238 mg, 2 mmol, 3.5 equiv.), 1,4-dioxane (5 ml) and water (1 ml) was stirred at 100° C. under a nitrogen atmosphere for 15 h. The reaction mixture was allowed to cool down to room temperature and concentrated to give a residue. The residue was purified by silica gel chromatography (CH2Cl2/methanol 500:1 to 100:1 as eluent) to afford title compound N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-(thiophen-2-yl)pyrimidin-4-amine (Compound 27)(92.2 mg, 50.9%) as solid. LC-MS (m/z)=284.0 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.71 (m, 2H), 0.95 (m, 2H), 1.94 (m, 1H), 6.35 (s, 1H), 6.87 (s, 1H), 7.17 (m, 1H), 7.70 (m, 1H), 7.83 (d, J=2.8 Hz, 1H), 8.23 (d, J=5.6 Hz, 1H), 9.91 (s, 1H), 12.08 (s, 1H).

Provenance & Evidence