Potassium Carbonate → HCID 71186588, compound

HRID 633617Notes

Reaction equation

HRID 633617 reaction equation
C(=O)([O-])[O-].[K+].[K+].CS([C:11]1[N:12]=[C:13]([CH2:37][CH2:38][CH3:39])[C:14]2[N:19]=[C:18]([C:20]3[CH:34]=[C:33]([CH3:35])[C:23]([O:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[C:22]([CH3:36])[CH:21]=3)[O:17][C:15]=2[N:16]=1)(=O)=O.[F:40][C:41]1[CH:46]=[CH:45][C:44]([F:47])=[CH:43][C:42]=1[OH:48]>CN1C(=O)CCC1.C(OCC)(=O)C>[F:40][C:41]1[CH:46]=[CH:45][C:44]([F:47])=[CH:43][C:42]=1[O:48][C:11]1[N:12]=[C:13]([CH2:37][CH2:38][CH3:39])[C:14]2[N:19]=[C:18]([C:20]3[CH:34]=[C:33]([CH3:35])[C:23]([O:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[C:22]([CH3:36])[CH:21]=3)[O:17][C:15]=2[N:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 949522,5-DifluorophenolHCID 71186232HCID 71186232, compound

Product 1

HCID 71186588HCID 71186588, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

68 mg of potassium carbonate were added to a solution of 107 mg of tert-butyl [4-(5-methanesulfonyl-7-propyloxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate in 1.1 ml of NMP, and 32 mg of 2,5-difluorophenol were then added. The reaction mixture was heated in a microwave synthesizer to 110° C. for 5 min and then cooled and poured onto ice. The precipitated compound was taken up in ethyl acetate, washed with water until neutral, dried over sodium sulfate, filtered and concentrated. The crude product was chromatographed on silica gel (heptane/ethyl acetate), giving 45 mg (38%) of the title compound.

Workup

  1. additionwere then added
  2. temperaturecooled
  3. additionpoured onto ice
  4. washwashed with water until neutral,
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was chromatographed on silica gel (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-8fa5ddbbd4624379a2650de990b0a63a
Source dataset
uspto-grants-2016_04
Patent number
US09321787B2

Reaction notes

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