Water → HCID 178518395, compound

HRID 475870Notes

Reaction equation

HRID 475870 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].O=[C:6]1[CH:10]([C:11]2[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)[CH2:9][CH2:8][CH:7]1[C:21](OCC)=[O:22].O>CO>[F:19][C:17]([F:18])([F:20])[C:14]1[N:13]=[CH:12][C:11]([CH:10]2[C:6]3[N:1]=[C:2]([OH:3])[N:4]=[C:21]([OH:22])[C:7]=3[CH2:8][CH2:9]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1176UreaHCID 58075576HCID 58075576, compound

Product 1

HCID 178518395HCID 178518395, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a melt of urea (748 mg, 12.45 mmol) at 150° C. was added ethyl 2-oxo-3-(6-(trifluoromethyl)pyridin-3-yl)cyclopentanecarboxylate (750 mg, 2.49 mmol) dropwise. The reaction was stirred overnight. The reaction mixture was cooled and the resulting solid mass was broken up and suspended in MeOH. The mixture was diluted with a large excess of water and cooled in an ice bath. The suspension was filtered and the residue was washed with water and dried to afford the semi-pure product, 7-(6-(trifluoromethyl)pyridin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol (334 mg, 1.124 mmol, 45.1% yield). LC-MS (M+H)+=298.0.

Workup

  1. temperatureThe reaction mixture was cooled
  2. temperaturecooled in an ice bath
  3. filtrationThe suspension was filtered
  4. washthe residue was washed with water
  5. customdried

Sources & evidence

ORD record
ord-d61acb9f655e4281b1de5afbff034be6
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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