Cesium carbonate → HCID 11526494, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of isopropyl 4-(6-chloro-5-methoxypyrimidin-4-yloxy)piperidine-1-carboxylate (78.5 mg, 0.238 mmol), 2-methyl-6-(2-(methylsulfonyl)propan-2-yl)pyridin-3-amine (54.3 mg, 0.238 mmol), Pd2(dba)3 (20.0 mg, 0.0218 mmol), biphenyl-2-yl-di-tert-butyl-phosphane (3.0 mg, 0.0101 μmol), and cesium carbonate (160 mg, 0.491 mmol) in 4M dioxane were heated under microwave irradiation at 100° C. Mixture was purified by HPLC; fractions containing product were partly concentrated, and residue was extracted with CH2Cl2 and 1M NaHCO3. Organic phases were dried over MgSO4, filtered, and concentrated to give isopropyl 4-(5-methoxy-6-(2-methyl-6-(2-(methylsulfonyl)propan-2-yl)pyridin-3-ylamino)pyrimidin-4-yloxy)piperidine-1-carboxylate (4.6 mg, 4%) as a white solid. 1HNMR (CDCl3, 400 MHz) δ 1.16-1.17 (d, J=6.3 Hz, 6H), 1.80-1.86 (m, 2H), 1.87 (s, 6H), 2.01-2.06 (m, 2H), 2.56 (s, 3H), 2.81 (s, 3H), 3.38-3.44 (m, 2H), 3.77-3.82 (m, 2H), 3.96 (s, 3H), 4.91-4.97 (m, 1H), 5.35-5.39 (m, 1H), 6.98 (s, 1H), 7.51-7.53 (d, J=8.6 Hz, 1H), 8.13 (s, 1H), 8.51-8.53 (d, J=8.6 Hz, 1H). Exact mass calculated for C24H35N5O6S 521.23 found 522.5 (MH+).

Provenance & Evidence