2-(4-hydroxy-2-methylphenyl)-N,N-dimethylacetamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[4-(benzyloxy)-2-methylphenyl]-N,N-dimethylacetamide (680 mg, 2.40 mmol) was dissolved in ethanol (4 ml). and palladium hydroxide on carbon (20%) (169 mg, 0.240 mmol) added. The mixture was stirred under an atmosphere of hydrogen gas at RT overnight. The mixture was filtered and the filtrate concentrated under reduced pressure to afford the title compound. LC/MS (m/z): 194 (M+H)+. The mixture was filtered the filtrate concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanol (90 mg, 0.319 mmol) was dissolved in toluene (1 ml) and 2-(4-hydroxy-2-methylphenyl)-N,N-dimethylacetamide (62 mg, 0.319 mmol), triphenylphosphine (126 mg, 0.479 mmol), and DIAD (93 μl, 0.479 mmol) added and the mixture stirred at RT overnight. The mixture was concentrated in vacuo and the residue purified by chromatography using a Biotage RP C18 cartridge (30 g) using a gradient eluant of 10-100% water:acetonitrile+0.1% TFA to afford the title compound. LC/MS (m/z): 457 (M+H)+. GPR119 Human EC50: 1.7 nM. The mixture was concentrated in vacuo the residue purified by chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[4-(benzyloxy)-2-methylphenyl]-N,N-dimethylacetamide (680 mg, 2.40 mmol) was dissolved in ethanol (4 ml) and palladium hydroxide on carbon (20%) (169 mg, 0.240 mmol) added. The mixture was stirred under an atmosphere of hydrogen gas at RT overnight. The mixture was filtered and the filtrate concentrated under reduced pressure to afford the title compound. LC/MS (m/z): 194 (M+H)+. The mixture was filtered the filtrate concentrated under reduced pressure