Water → HCID 178429745, compound

HRID 714416Notes

Reaction equation

HRID 714416 reaction equation
[F:1][C:2]1[C:3]([CH3:31])=[C:4]([N:8]2[C:13](=[O:14])[C:12]([C:15](OC3CCCC(=O)C=3)=[O:16])=[CH:11][N:10]=[C:9]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:5]=[CH:6][CH:7]=1.[F-].[Cs+].[OH2:34].C([O:38][CH2:39][CH3:40])(=O)C>C(#N)C>[F:1][C:2]1[C:3]([CH3:31])=[C:4]([N:8]2[C:13](=[O:14])[C:12]([C:15]([C:6]3[C:7](=[O:34])[CH2:2][CH2:3][CH2:40][C:39]=3[OH:38])=[O:16])=[CH:11][N:10]=[C:9]2[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25953Cesium fluorideHCID 67955156HCID 67955156, compound

Product 1

HCID 178429745HCID 178429745, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-oxo-1-cyclohexen-1-yl 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate (i.e. the product from Example 5, Step C) (42 g, 100.4 mmol) in acetonitrile (200 mL) was added cesium fluoride (30.5 g, 200.8 mmol). The reaction mixture was stirred for 24 h at room temperature. Water and ethyl acetate was added to the reaction mixture and the water layer was extracted several times with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting solid was washed several times with ether and filtered, followed by the addition 60 mL of ethyl acetate and let stir for 2 h. The resulting solid was then washed again with ether and dried under reduced pressure to afford the title product, a compound of the present invention, as a yellow solid (26 g).

Workup

  1. extractionthe water layer was extracted several times with ethyl acetate
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. washThe resulting solid was washed several times with ether
  5. filtrationfiltered
  6. additionfollowed by the addition 60 mL of ethyl acetate
  7. stirringlet stir for 2 h
  8. washThe resulting solid was then washed again with ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-9d970360a1a644368aa5ef6594537f3a
Source dataset
uspto-grants-2015_11
Patent number
US09187432B2

Reaction notes

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