Trifluoroacetic acid → 1-(4-Hydroxy-butyl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione

HRID 12658Notes

Reaction equation

HRID 12658 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[C:14](=[O:21])[NH:13][C:12]1=[O:22])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH:16]=[C:15]([C:17]([F:18])([F:19])[F:20])[C:14](=[O:21])[NH:13][C:12]1=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 686939601-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-5-trifluoromethyl-1H-pyrimidine-2,4-dione

Product 1

HCID 589942241-(4-Hydroxy-butyl)-5-trifluoromethyl-1H-pyrimidine-2,4-dioneYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-5-trifluoromethyl-1H-pyrimidine-2,4-dione (Prep22, 260 mg, 0.71 mmol) in DCM (15 mL) was cooled at 0° C. and then TFA (820 μl, 1.1 mmol) was added. The mixture was stirred for 1 hour at room temperature and the solvent was evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (7-3) to afford the title compound (132 mg, 74% yield).

Workup

  1. customthe solvent was evaporated
  2. customThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (7-3)

Sources & evidence

ORD record
ord-fe9abdc192c54b518602509531500c56
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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