Sodium borohydride → 3-[2-Amino-6-(hydroxy-phenyl-methyl)-4H-quinazolin-3-yl]-N-cyclohexyl-N-methyl-propionamide

HRID 2088816Notes

Reaction equation

HRID 2088816 reaction equation
[NH2:1][C:2]1[N:11]([CH2:12][CH2:13][C:14]([N:16]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:17])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:8]=2)[N:3]=1.[BH4-].[Na+]>CO.C1COCC1>[NH2:1][C:2]1[N:11]([CH2:12][CH2:13][C:14]([N:16]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:17])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:24]([OH:31])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 167412383-(2-Amino-6-benzoylquinazolin-3(4H)-YL)-N-cyclohexyl-N-methylpropanamide

Product 1

HCID 586251343-[2-Amino-6-(hydroxy-phenyl-methyl)-4H-quinazolin-3-yl]-N-cyclohexyl-N-methyl-propionamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(2-amino-6-benzoyl-4H-quinazolin-3-yl)-N-cyclohexyl-N-methyl-propionamide (0.0056 mol) in methanol (60 mL) and THF (30 mL) was stirred at room temperature. Then, NaBH4 (0.0056 mol) was added and the reaction mixture was stirred for 30 min at room temperature. The solvent was evaporated, and the residue was stirred in H2O and then extracted with CH2Cl2. The organic layer was separated and dried, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: 94:6 CH2Cl2:(CH3OH:NH3)). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. stirringthe reaction mixture was stirred for 30 min at room temperature
  2. customThe solvent was evaporated
  3. stirringthe residue was stirred in H2O
  4. extractionextracted with CH2Cl2
  5. customThe organic layer was separated
  6. customdried
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: 94:6 CH2Cl2:(CH3OH:NH3))
  9. customThe purest product fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-288c8fcca4444ab3a2a36e27f60198c1
Source dataset
uspto-grants-2013_05
Patent number
US08436006B2

Reaction notes

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