Acetone → HCID 136247202, compound

HRID 1022443Notes

Reaction equation

HRID 1022443 reaction equation
[CH2:1]([N:5]1[C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[NH:12][C:13](=[O:14])[C:8]=2[CH:7]=[CH:6]1)CC=C.[Mn]([O-])(=O)(=O)=[O:26].[K+].[CH3:31][C:32]([CH3:34])=[O:33]>O>[OH:33][CH:32]([CH2:34][OH:26])[CH2:31][CH2:1][N:5]1[C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[NH:12][C:13](=[O:14])[C:8]=2[CH:7]=[CH:6]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 516875Potassium PermanganateHCID 136247182HCID 136247182, compound

Product 1

HCID 136247202HCID 136247202, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7-but-3-enyl-2-(4-trifluoromethyl-phenyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (50.3 mg, 151 μmol) in acetone (1.2 mL) and water (0.4 mL) was treated with potassium permanganate (46.1 mg, 292 μmol). The reaction stirred at room temperature overnight. The reaction was filtered through a coarse sintered glass frit, rinsing with ethyl acetate. The filtrate was concentrated in vacuo and then partitioned between water (25 mL) and ethyl acetate (25 mL). The aqueous layer was back extracted with ethyl acetate (25 mL), and the combined organics were washed with a saturated aqueous sodium chloride solution (25 mL), dried over magnesium sulfate, filtered and rinsed with ethyl acetate, and concentrated in vacuo. Flash chromatography (24 g silica gel column, 1-10% methanol/methylene chloride) afforded 7-(3,4-dihydroxy-butyl)-2-(4-trifluoromethyl-phenyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one as a white solid (6.9 mg, 12.4%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.72 (s, 1H) 1.85-2.15 (m, 1H) 3.10-3.53 (m, 3H) 4.09-4.45 (m, 2H) 4.48-4.62 (m, 1H) 4.72 (d, J=5.09 Hz, 1H) 6.53 (d, J=3.20 Hz, 1H) 7.12-7.34 (m, 1H) 7.90 (d, J=8.29 Hz, 2H) 8.34 (d, J=8.48 Hz, 2H) 12.3.1 (s, 1H). LC-MS calcd. for C17H17F3N3O3 [(M+H)+] 368, obsd. 368.0.

Workup

  1. filtrationThe reaction was filtered through a coarse sintered glass frit
  2. washrinsing with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompartitioned between water (25 mL) and ethyl acetate (25 mL)
  5. extractionThe aqueous layer was back extracted with ethyl acetate (25 mL)
  6. washthe combined organics were washed with a saturated aqueous sodium chloride solution (25 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. washrinsed with ethyl acetate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46aab6f60a704372b07601c3c6776a7b
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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