Cesium carbonate → 4-(5-(2-cyclopropyl-1H-benzo[d]imidazol-1-yl)-2-((3-(tetrahydro-2H-pyran-4-yl)azetidin-1-yl)methyl)thiazolo[5,4-d]pyrimidin-7-yl)morpholine

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A mixture of 5-chloro-7-morpholin-4-yl-2-[3-(tetrahydropyran-4-yl)azetidin-1-ylmethyl]thiazolo[5,4-d]pyrimidine (90 mg, 0.22 mmol), 2-cyclopropylbenzimidazole (42 mg, 0.26 mmol), tris(dibenzylideneacetone)dipalladium (10 mg, 0.01 mmol), Xphos (21 mg, 0.04 mmol) and Cs2CO3 (143 mg, 0.44 mmol) in dioxane (2.5 mL) was purged with argon then heated at 145° C. for 30 min in a microwave reactor. The reaction mixture was filtered through a pad of celite, washing with EtOAc. The filtrate was concentrated in vacuo and purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-7%). The resulting residue was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH/DCM and the product eluted with 2M NH3/MeOH affording 484 as an orange solid (83 mg, 71%). LCMS (Method I): RT 2.89 min, [M+H]+ 532.2. 1H NMR (CDCl3, 400 MHz): δ 7.94-7.89 (m, 1 H); 7.69-7.65 (m, 1 H); 7.26-7.20 (m, 2 H); 4.43 (m, 4 H); 3.99 (m, 4 H); 3.87 (m, 4 H); 3.61 (m, 2 H); 3.38 (m, 2 H); 3.10 (m, 2 H); 2.89-2.82 (m, 1 H); 2.36 (m, 1 H); 1.71 (m, 1 H); 1.56 (m, 2 H); 1.37-1.31 (m, 2 H); 1.30-1.18 (m, 2 H) and 1.10-1.04 (m, 2 H)

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