Water → HCID 10002668, compound

HRID 1656534Notes

Reaction equation

HRID 1656534 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:23][C:24]([NH:26][CH:27]([CH:34]([CH3:36])[CH3:35])[C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])=[O:25])[C:10](=[O:22])[C:11]([N:14](C(=O)C(F)(F)F)[CH3:15])=[CH:12][N:13]=2)=[CH:4][CH:3]=1.O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:23][C:24]([NH:26][CH:27]([CH:34]([CH3:36])[CH3:35])[C:28](=[O:33])[C:29]([F:30])([F:32])[F:31])=[O:25])[C:10](=[O:22])[C:11]([NH:14][CH3:15])=[CH:12][N:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 19787891HCID 19787891, compound

Product 1

HCID 10002668HCID 10002668, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[2-(4-fluorophenyl)-5-(N-trifluoroacetyl-N-methylamino)-6-oxo-1,6-dihydro-1-pyrimidinyl]-N-(3,3,3,-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.58 g) in tetrahydrofuran (5 mL) was added water (10 mL) followed by potassium carbonate (0.76 g). The mixture was stirred overnight, extracted into dichloromethane, washed (water, brine), dried (MgSO4) and evaporated. The residue was purified by chromatography, with dichloromethane:methanol (gradient, 99.5:0.5, 98.5:1.5) as the eluent, to give the title compound; TLC: Rf =0.34, dichloromethane:methanol (98:2); NMR: 0.70-1.0 (m,6), 2.03-2.33 (m,1), 2.71 (d,3), 4.00-4.70 (m,3), 5.63-5.73 (m,1), 7.03 (s,1), 7.17-7.30 (m,2), 7.43-7.60 (m,2), 8.81 (d,1); MS: m/z=429(M+1).

Workup

  1. extractionextracted into dichloromethane
  2. washwashed (water, brine)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by chromatography, with dichloromethane

Sources & evidence

ORD record
ord-09e809bc354b48fcafe565c3c0b3143d
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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