Potassium Carbonate → HCID 178497582, compound

Participants

Reaction Conditions

Reaction Steps

6-chloro-N4-(trans-3-(quinazolin-2-ylamino)cyclobutyl)pyrimidine-4,5-diamine (from example 13 step 2, 0.045 g, 0.132 mmol), tetrakis(triphenylphosphine)palladium (0.015 g, 0.013 mmol), (4-methoxycarbonylphenyl)boronic acid (0.036 g, 0.197 mmol), and potassium carbonate (0.073 g, 0.527 mmol) were combined with dioxane (2 mL) and water (0.5 mL) and sealed in a vial under argon. The reaction was heated at 120° C. for 25 minutes in the microwave. The crude product was partitioned between water (100 mL) and ethyl acetate (100 mL) and the organic phase dried with magnesium sulfate. Purification using silica chromatography (0-8% (2N ammonia in methanol) in dichloromethane) gave the desired methyl 4-(5-amino-6-((trans-3-(quinazolin-2-ylamino)cyclobutyl)amino)pyrimidin-4-yl)benzoate (0.039 g, 0.088 mmol, 67.1% yield) as a yellow oil.

Provenance & Evidence