Boric Acid → HCID 89815811, compound

HRID 717569Notes

Reaction equation

HRID 717569 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][CH:4]=[N:3]1.[BH4-].[Na+].B(O)(O)O>CO>[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][CH2:4][NH:3]1

Participants

5

Reactant 3

HCID 7628Boric AcidHCID 4311764Sodium borohydrideHCID 89816095HCID 89816095, compound

Product 1

HCID 89815811HCID 89815811, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-methyl-5-phenyl-1,4-dihydropyrimido[4,5-c]pyridazine (350 mg) in dry methanol (15.0 mL), sodium borohydride (296 mg, 7.81 mmol) was added slowly, followed by boric acid (480 mg) under nitrogen atmosphere at 0° C. The reaction mixture was stirred at room temperature for 24 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 EtOAc/hexane (1.4:8.6) as eluent to afford 1-methyl-5-phenyl-1,2,3,4-tetrahydropyrimido[4,5-c]pyridazine (130 mg) as gummy liquid. 1H NMR (DMSO-d6): δ 2.66-2.69 (t, 2H), 2.88-2.91 (t, 2H), 3.22 (s, 3H), 5.46-5.50 (t, 1H), 7.41-7.47 (m, 3H), 7.53-7.55 (m, 2H), 8.36 (s, 1H).

Workup

  1. customsolvents were removed under reduced pressure
  2. additionThe resulting oil was diluted with dichloromethane (50 mL)
  3. washwashed with 10% NaHCO3 (10 mL) and brine (10 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give a residue which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-8528be4beb57495c9a3e2af550373abb
Source dataset
uspto-grants-2015_11
Patent number
US09193725B2

Reaction notes

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