Triacetoxyperiodinane → HCID 178422979, compound

HRID 625762Notes

Reaction equation

HRID 625762 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:21])[C:9]2[N:18]=[C:17]([OH:19])[C:16]3[C:11](=[CH:12][C:13]([CH3:20])=[CH:14][CH:15]=3)[N:10]=2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:9]2[N:18]=[C:17]([OH:19])[C:16]3[C:11](=[CH:12][C:13]([CH3:20])=[CH:14][CH:15]=3)[N:10]=2)=[O:21])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 1784229802-[(4-fluorophenyl)-hydroxymethyl]-7-methyl-1H-quinazolin-4-one

Product 1

HCID 178422979HCID 178422979, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-((4-fluorophenyl)(hydroxy)methyl)-7-methylquinazolin-4-ol (3 g, 10.56 mmol) in acetonitrile (45 mL) was added Dess-Martin periodinane (5.37 g, 12.67 mmol), and the mixture was stirred at rt for 5 h. Saturated sodium hydrogen carbonate solution was then added and the mixture was stirred at rt overnight. This suspension was then filtered and the resulting solid dried to give crude (4-fluorophenyl)(4-hydroxy-7-methylquinazolin-2-yl)methanone (2.65 g, 89%). LC-MS (ESI) m/z 283 (M+H)+.

Workup

  1. stirringthe mixture was stirred at rt overnight
  2. filtrationThis suspension was then filtered
  3. customthe resulting solid dried

Sources & evidence

ORD record
ord-3cd08acf61ac4f2c9d8cd973a5206166
Source dataset
uspto-grants-2016_04
Patent number
US09308207B2

Reaction notes

Loading…