Ammonium Chloride → HCID 57678400, compound

Participants

Reaction Conditions

Reaction Steps

5-(2,5-Diiodo-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (1.2 g, 2.5 mmol), bis(triphenylphosphine)palladium dichloride (175 mg, 2.5 mmol), and CuI (25 mg, 0.125 mmol) were added to 7 mL dry THF. Trimethylsilylacetylene ((0.48 mL, 3.3 mmol), and diisopropylethylamine (3.5 mL) were added, and the reaction mixture was heated to 50° C. under nitrogen for 27 hours. The reaction mixture was cooled, poured into 15% aqueous NH4Cl and extracted into EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give crude 5-(4-Methoxy-2,5-bis-trimethylsilanylethynyl-phenoxy)-pyrimidine -2,4-diamine together with monoacetylenes 5-(2-iodo-4-methoxy-5-trimethylsilanylethynyl-phenoxy)-pyrimidine-2,4-diamine and 5-(5-iodo-4-methoxy-2-trimethylsilanylethynyl-phenoxy)-pyrimidine-2,4-diamine. This residue was chromatographed on 125 g of flash silica (6:1:1 CH2Cl2:MeOH:NH4OH) to give 450 mg of 5-(4-Methoxy-2,5-bis-trimethylsilanylethynyl-phenoxy)-pyrimidine-2,4-diamine, MS (M+H)=425.

Provenance & Evidence