Trifluoroacetic acid → 1-(3-Hydroxy-propyl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione

HRID 12656Notes

Reaction equation

HRID 12656 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[C:13](=[O:20])[NH:12][C:11]1=[O:21])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[C:13](=[O:20])[NH:12][C:11]1=[O:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 686942291-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-5-trifluoromethyl-1H-pyrimidine-2,4-dione

Product 1

HCID 589942071-(3-Hydroxy-propyl)-5-trifluoromethyl-1H-pyrimidine-2,4-dioneYield 57.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-5-trifluoromethyl-1H-pyrimidine-2, 4-dione (Prep 19, 0.86 g, 2.4 mmol) in DCM (10 mL) was cooled at 0° C. and then TFA (2.8 mL, 36 mmol) was added. The mixture was stirred for 1 hour at room temperature and then the solvent was evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (7-3) to afford the title compound (0.33 g, 57% 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-ccb073e46e534ab58490533d67947800
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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