Urea → HCID 178469855, compound

HRID 131292Notes

Reaction equation

HRID 131292 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:13][C:14]([NH2:16])=[O:15].[CH:17]([O-])([O-])OCC>C1(C)C(C)=CC=CC=1>[OH:15][C:14]1[N:16]=[C:3]([C:2]([F:12])([F:11])[F:1])[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:17][N:13]=1

Participants

5

Reactant 3

HCID 1176UreaHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 53630039Ethylorthoformate

Product 1

HCID 178469855HCID 178469855, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of ethyl 4,4,4-trifluoroacetoacetate (23.1 g), urea (7.54 g) and ethyl orthoformate (18.6 g) is stirred at 130° C. under argon gas atmosphere for 1.5 hours. To the reaction mixture is added xylene (100 mL) and the mixture is stirred at 140° C. for 17 hours. The reaction mixture is evaporated to remove solvent and the residue is diluted with methanol. The solution is treated with an activated carbon powder, concentrated in vacuo, and triturated in diisopropylether to give ethyl 2-hydroxy-4-trifluoromethyl-5-pyrimidinecarboxylate (20.3 g, yield; 69%) as crystals. MS (ESI) m/z; 235 [M−H]−

Workup

  1. stirringthe mixture is stirred at 140° C. for 17 hours
  2. customThe reaction mixture is evaporated
  3. customto remove solvent
  4. additionthe residue is diluted with methanol
  5. additionThe solution is treated with an activated carbon powder
  6. concentrationconcentrated in vacuo
  7. customtriturated in diisopropylether

Sources & evidence

ORD record
ord-743c2e459c6f4e37beb7f7a6c2460152
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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