Water → 4-(4-Fluoro-phenyl)-2-isopropyl-5,6,7,8-tetrahydro-quinazolin-7-ol

HRID 1917265Notes

Reaction equation

HRID 1917265 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[CH2:16][CH2:15][C:14](=[O:18])[CH2:13][C:12]=3[N:11]=[C:10]([CH:19]([CH3:21])[CH3:20])[N:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].[OH-].[Na+].O>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[CH2:16][CH2:15][CH:14]([OH:18])[CH2:13][C:12]=3[N:11]=[C:10]([CH:19]([CH3:21])[CH3:20])[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 666163744-(4-fluoro-phenyl)-2-isopropyl-5,8-dihydro-6H-quinazolin-7-one

Product 1

HCID 578812264-(4-Fluoro-phenyl)-2-isopropyl-5,6,7,8-tetrahydro-quinazolin-7-olYield 772.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(4-fluoro-phenyl)-2-isopropyl-5,8-dihydro-6H-quinazolin-7-one (0.126 g) in EtOH (3 mL) was added NaBH4 (0.053 g). After 16 h, the mixture was treated with 1 M NaOH (5 mL) and water (10 mL). The mixture was stirred for 30 min then extracted with CH2Cl2. The organic layer was dried and concentrated. Chromatography on SiO2 (10 to 35% EtOAc/hexanes) afforded 0.98 g of the title compound. TLC (SiO2, 50% EtOAc/hexanes): Rf=0.18. MS (ESI): exact mass calcd. for C17H19FN2O, 286.15; m/z found, 287.3 [M+H]+.

Workup

  1. extractionthen extracted with CH2Cl2
  2. customThe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-59bfde1958524802866ef0cd6c7a8e0d
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Reaction notes

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