Diisopropylamine → HCID 20732840, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 300 mg (0.648 mmol) of 4-(6-iodo-4-oxo-4H-quinazolin-3-ylmethyl)-benzoic acid tert-butyl ester (preparation described above) in 50 mL of dimethylformamide (“DMF”), was added diisopropylamine (4 mol eq.), a catalytic amount of CuI, 4-prop-2-ynyl-morpholine (4 mol eq.), and Pd(PPh3)2Cl2 (a catalytic amount). The reaction mixture was then heated to 50° C. for 15 hours. The reaction was then diluted with 200 mL of EtOAc, and washed with 2×200 mL water, and 1×200 mL brine. The organic layer was dried over MgSO4 and concentrated. The residue was then passed through a silica gel column, elution with 4:1 EtOAc:tetrahydrofuran (“THF”). The product is carried directly to the next step.

Provenance & Evidence