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

HRID 717582Notes

Reaction equation

HRID 717582 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH2:9]Cl)=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[CH:4][N:3]=1.[NH2:17][NH2:18]>C1COCC1>[C:11]1([C:6]2[N:5]=[CH:4][N:3]=[C:2]3[NH:17][NH:18][CH2:9][CH2:8][C:7]=23)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 898145964-Chloro-5-(2-chloroethyl)-6-phenylpyrimidine

Product 1

HCID 898158305-Phenyl-1,2,3,4-tetrahydropyridazino[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

  1. customsolvents were removed under reduced pressure
  2. customThe resulting oil was purified by column chromatography

Sources & evidence

ORD record
ord-594751323e76465398efeffe3c8c2a7a
Source dataset
uspto-grants-2015_11
Patent number
US09193725B2

Reaction notes

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