Hydrazine → 5-Phenyl-1,2,3,4-tetrahydropyridazino[3,4-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-chloro-5-(2-chloroethyl)-6-phenylpyrimidine (150 mg) in dry THF (10 mL), hydrazine (5 mL, 1.0M in THF) was slowly added under nitrogen atmosphere at room temperature. The reaction mixture was stirred at 60° C. for 5 hours and solvents were removed under reduced pressure. The resulting oil was purified by column chromatography using MeOH/CHCl3 (0.5:9.5) as eluent to afford 5-phenyl-1,2,3,4-tetrahydropyridazino[3,4-d]pyrimidine (45 mg) as colorless oily liquid. 1H NMR (DMSO-d6): δ 2.63-2.65 (t, 2H), 2.79-2.81 (t, 2H), 4.93-4.97 (t, 1H), 7.43-7.48 (m, 3H), 7.56-7.59 (m, 2H), 8.29 (s, 1H), 8.69 (s, 1H).

Provenance & Evidence