Dimethylformamide → HCID 59605806, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-9-methyl-6-morpholin-4-yl-8-[3-(tetrahydropyran-4-yl)azetidin-1-ylmethyl]-9H-purine (120 mg, 0.29 mmol), (1H-benzoimidazol-2-yl)methylamine (52 mg, 0.35 mmol), tris(dibenzylideneacetone)dipalladium (14 mg, 0.01 mmol), Xphos (28 mg, 0.06 mmol) and Cs2CO3 (192 mg, 0.59 mmol) in DMF (2.5 mL) was purged with argon then heated at 150° 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, 0-15%) affording 435 as a foam (104 mg, 69%). LCMS (Method I): RT 2.45 min, [M+H]+ 518.4. 1H NMR (CDCl3, 400 MHz): δ 8.48 (d, J=5.0 Hz, 1 H); 8.28 (d, J=8.0 Hz, 1 H); 7.49 (d, J=7.8 Hz, 1 H); 7.19 (m, 1 H); 7.10-7.04 (m, 1 H); 4.34 (m, 4 H); 3.97 (dd, J=11.5, 4.1 Hz, 2 H); 3.90 (t, J=4.7 Hz, 4 H); 3.85 (s, 3 H); 3.82 (s, 2 H); 3.51 (t, J=7.3 Hz, 2 H); 3.42-3.32 (m, 2 H); 3.26 (d, J=5.0 Hz, 3 H); 3.03 (t, J=7.0 Hz, 2 H); 2.34-2.25 (m, 1 H); 1.74-1.62 (m, 1 H); 1.54 (m, 2 H) and 1.27-1.13 (m, 2 H)

Provenance & Evidence