2-Fluorophenol → HCID 53311546, compound

HRID 1626027Notes

Reaction equation

HRID 1626027 reaction equation
C(=O)([O-])[O-].[K+].[K+].CS([C:11]1[N:12]=[C:13]([O:30][CH:31]2[CH2:34][O:33][CH2:32]2)[C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[C:24]([CH3:26])[C:23]([O:27][CH3:28])=[C:22]([CH3:29])[CH:21]=3)[O:17][C:15]=2[N:16]=1)(=O)=O.[F:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[OH:42]>CN(C=O)C>[F:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[O:42][C:11]1[N:12]=[C:13]([O:30][CH:31]2[CH2:34][O:33][CH2:32]2)[C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[C:24]([CH3:26])[C:23]([O:27][CH3:28])=[C:22]([CH3:29])[CH:21]=3)[O:17][C:15]=2[N:16]=1

Participants

5

Reactant 3

HCID 97072-FluorophenolHCID 11430Potassium CarbonateHCID 67324439HCID 67324439, compound

Product 1

HCID 53311546HCID 53311546, compoundYield 143.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

410 mg of potassium carbonate and 547 mg of 5-methanesulfonyl-2-(4-methoxy-3,5-dimethyl-phenyl)-7-(oxetan-3-yloxy)-oxazolo[5,4-d]pyrimidine were added to a solution of 49 mg of 2-fluorophenol in 8 ml of DMF. The mixture was stirred at room temperature for 2 h. After filtration, the solvent was distilled off in vacuo, and the product was isolated by silica gel chromatography (heptane/ethyl acetate gradient) to yield 275 mg of the title compound.

Workup

  1. filtrationAfter filtration
  2. distillationthe solvent was distilled off in vacuo
  3. customthe product was isolated by silica gel chromatography (heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-8e223eba80554ee9989c676872d833f3
Source dataset
uspto-grants-2014_07
Patent number
US08785439B2

Reaction notes

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