Cesium carbonate → (5-(2-ethyl-1H-benzo[d]imidazol-1-yl)-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)(4-(2-hydroxypropan-2-yl)piperidin-1-yl)methanone

Participants

Reaction Conditions

Reaction Steps

A mixture of (5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-yl)-[4-(1-hydroxy-1-methylethyl)piperidin-1-yl]methanone (250 mg, 0.59 mmol), 2-ethylbenzimidazole (90 mg, 0.62 mmol), tris(dibenzylideneacetone)dipalladium (15 mg, 2.5 mol %), XPhos (25 mg, 10 mol %) and Cs2CO3 (270 mg, 0.83 mmol) in DMF (6 mL) was purged with argon then heated at 150° C. for 30 min in a microwave reactor. The reaction mixture was purified by column chromatography (Si-PCC, MeOH:DCM, 1-5%) followed by recrystallisation from Et2O and EtOAc affording 771 (109 mg, 35%). LCMS (method I): RT 3.96 min [M+H]+ 536.3. 1H NMR (CDCl3, 400 MHz): δ 8.06-8.05 (1 H, m), 7.76-7.75 (1 H, m), 7.32-7.28 (2 H, m), 5.22 (1 H, d, J=13.34 Hz), 4.84 (1 H, d, J=13.16 Hz), 4.41 (4 H, brd s), 3.89 (4 H, t, J=4.74 Hz), 3.37 (2 H, q, J=7.46 Hz), 3.17-3.15 (1 H, m), 2.84-2.82 (1 H, m), 1.94 (2 H, t, J=13.72 Hz), 1.72-1.62 (1 H, m), 1.49-1.40 (5 H, m), 1.23 (6 H, d, J=7.01 Hz)

Provenance & Evidence