Boric Acid → HCID 89815916, compound
Reaction equation
[CH3:1][N:2]1[C:7]2=[N:8][CH:9]=[N:10][C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:6]2[CH2:5][C:4]([CH3:18])=[N:3]1.[BH4-].[Na+].B(O)(O)O>C1COCC1>[CH3:1][N:2]1[C:7]2=[N:8][CH:9]=[N:10][C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:6]2[CH2:5][CH:4]([CH3:18])[NH:3]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1,3-dimethyl-5-phenyl-1,4-dihydropyridazino[3,4-d]pyrimidine (260 mg) in dry THF (15 mL), sodium borohydride (414 mg) was slowly added, followed by boric acid (670 mg) under nitrogen atmosphere at 0° C. The reaction mixture was stirred at room temperature for 2 hours and solvents were removed under reduced pressure. The resulting oil was diluted with dichloromethane (50 mL), washed with 10% NaHCO3 (10 mL) and brine (10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to give a residue which was purified by column chromatography using MeOH/CHCl3 (0.5:9.5) as eluent to afford 1,3-dimethyl-5-phenyl-1,2,3,4-tetrahydropyridazino[3,4-d]pyrimidine (95 mg) as colorless oily liquid. 1H NMR (DMSO-d6): δ 1.00-1.02 (d, 3H), 2.62-2.71 (t, 2H), 3.22 (s, 3H), 3.31-3.34 (m, 1H), 5.28-5.31 (d, 1H), 7.43-7.51 (m, 5H), 8.36 (s, 1H).
Workup
- customsolvents were removed under reduced pressure
- additionThe resulting oil was diluted with dichloromethane (50 mL)
- washwashed with 10% NaHCO3 (10 mL) and brine (10 mL)
- dry with materialThe organic layer was dried over anhydrous Na2SO4
- concentrationconcentrated
- customto give a residue which
- customwas purified by column chromatography
Sources & evidence
- ORD record
- ord-bcf5572c86234d0294a740e9092053bd
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193725B2
Reaction notes
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