Potassium Carbonate → HCID 86685405, compound

HRID 570749Notes

Reaction equation

HRID 570749 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH3:10])[N:5]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[CH:13][CH:12]=2)[C:4](=[O:23])[CH:3]=1.[C:24](Cl)(=[O:27])[CH:25]=[CH2:26].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C(=O)C>[CH2:8]([C:6]1[N:5]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]([F:22])([F:20])[F:21])=[CH:15][CH:16]=2)[C:4](=[O:23])[C:3]2[CH2:26][CH2:25][C:24](=[O:27])[NH:1][C:2]=2[N:7]=1)[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 13140Acryloyl chlorideHCID 25517Ammonium ChlorideHCID 86685404HCID 86685404, compound

Product 1

HCID 86685405HCID 86685405, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 6-amino-2-propyl-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrimidin-4(3H)-one (270 mg) in N,N-dimethylacetamide (15 mL) was added acryloyl chloride (0.20 mL) at 0° C., and the mixture was stirred for 30 min, and then at room temperature overnight. To the reaction mixture was added potassium carbonate (570 mg) at room temperature, and the mixture was stirred for 1 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution under ice-cooling, and the mixture was extracted with a mixed solvent of ethyl acetate and THF. The extract was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (59.6 mg) as a solid.

Workup

  1. customat room temperature
  2. customovernight
  3. stirringthe mixture was stirred for 1 hr
  4. temperaturecooling
  5. extractionthe mixture was extracted with a mixed solvent of ethyl acetate and THF
  6. dry with materialThe extract was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e904d3a3a64a4d2e896558eb976f2827
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

Loading…