3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione → 3-(4-chloro-2-fluoro-5-hydroxyphenyl)6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 1450164Notes

Reaction equation

HRID 1450164 reaction equation
[Cl:1][C:2]1[C:7]([O:8]CC2C=CC=CC=2)=[CH:6][C:5]([N:16]2[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[NH:18][C:17]2=[O:27])=[C:4]([F:28])[CH:3]=1.[H][H]>[Pd].C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:16]2[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:24])([F:26])[F:25])[NH:18][C:17]2=[O:27])=[C:4]([F:28])[CH:3]=1

Participants

5

Reactant 2

HCID 199752623-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedioneHCID 178418361HCID 178418361, compound

Product 1

HCID 177702713-(4-chloro-2-fluoro-5-hydroxyphenyl)6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneYield 74.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4.27 g (10.3 mmol) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione and 420 mg of 10% palladium on charcoal in 70 mL of ethyl acetate was placed in a Paar bottle and was agitated under 45 psi hydrogen over a 16 hour period. It was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo and the resultant crude product flash chromatographed over silica gel, eluting with a 95:5 v:v mixture of dichloromethane and methanol to give 2.50 g of the title compound as a pale orange solid, m.p.: 68°-72° C.; 1H-NMR (DMSO-d6): ppm 7.5 (d, 1H), 7.0 (d, 1H), 6.4 (s, 1H).

Workup

  1. filtrationIt was filtered
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe resultant crude product flash chromatographed over silica gel
  5. washeluting with a 95:5 v
  6. additionv mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-31d8a8d7d0fe455598a20e7692eafe37
Source dataset
uspto-grants-1997_02
Patent number
US05602077

Reaction notes

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