Potassium Phosphate, Tribasic → 6-(4-(4,5-Dimethyl-1H-imidazol-2-YL)phenyl)-1-((tetrahydro-2H-pyran-4-YL)methyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

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Reaction Steps

6-(4-(4,5-Dimethyl-1H-imidazol-2-yl)phenyl)-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one 4,5-Dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazole (0.16 g, 0.53 mmol), 6-bromo-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (See Example 101.B) (0.168 g, 0.53 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.044 g, 0.053 mmol) and potassium phosphate (0.45 g, 2.14 mmol) were reacted in DMF (2 mL) according to General Procedure B2, except reaction was heated for 2 h. Purification by silica gel chromatography (10% methanol in ethyl acetate) gave the title compound as an off-white solid (40.0 mg, 19% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.1(s, 1H), 8.52(s, 1H), 8.06(d, J=8.6, 2H), 7.93 (d, J=8.20, 2H), 4.0-3.69(m, 4H), 3.26 (t, J=11.1, 2H), 2.2 (s, 3H), 2.15 (m, 1H), 2.05 (s,3H), 1.7 (m, 2H), 1.13 (m,2H); MS (ESI) m/z 405.4[M+1]+; mp 250-254° C. (dec.)

Provenance & Evidence