Sodium Carbonate → HCID 52934551, compound

Participants

Reaction Conditions

Reaction Steps

A 20 mL reaction vessel was charged with 2-(methylthio)-4-(4-phenoxyphenyl amino)pyrido[4,3-d]pyrimidin-5(6H)-one (221a, 182 mg, 0.48 mmol) and N-iodosuccinmide (158 mg, 0.70 mmol) in 8 mL dry DMF. The reaction mixture was stirred at 60° C. for 2 hours. The solvent was removed under reduced pressure yielding the pale brown solid (221b) after being recrystallized from acetonitrile (210 mg, 87%). A 20 mL reaction vessel was charged with 8-iodo-2-(methylthio)-4-(4-phenoxyphenylamino)pyrido[4,3-d]pyrimidin-5(6H)-one (221b, 52 mg, 0.10 mmol), benzenboronic acid (18 mg, 0.15 mmol), tetrakis(triphenyphosphine)palladium (0) (6 mg, 0.005 mmol), and 2.0 M aq. sodium carbonate solution in 6 ml dioxane. The mixture was purged with nitrogen for 30 min. Then the reaction mixture was heated at 80° C. for 3 h. The solvent was removed under reduced pressure yielding the brown residue. The residue was purified by silica gel chromatography using a gradient of 0-5% MeOH in dichloromethane yielding 221c. Then 221 was prepared as described in Example 1g starting from 2-(methylthio)-4-(4-phenoxyphenylamino)-8-phenylpyrido[4,3-d]pyrimidin-5(6H)-one, and 4-hydroxypiperidine to give title compound. MS m/z: 506 (M+H)+.

Provenance & Evidence