Ethyl 4,4,4-trifluoroacetoacetate → HCID 178498903, compound

HRID 846894Notes

Reaction equation

HRID 846894 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].CC[O:13][C:14]([CH2:16][C:17]([C:19]([F:22])([F:21])[F:20])=O)=O>O>[OH:13][C:14]1[N:6]2[N:5]=[CH:4][C:3]([C:7]([O:9][CH3:10])=[O:8])=[C:2]2[N:1]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=1

Participants

4

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 272904methyl 3-aminopyrazole-4-carboxylate

Product 1

HCID 178498903HCID 178498903, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 11.5 g of methyl 5-aminopyrazole-4-carboxylate, 16 ml of ethyl ω,ω,ω-trifluoroacetoacetate and 150 g of polyphosphoric acid was heated to 100° while stirring for 16 hours. After cooling to 20°, cold water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with 1N aqueous hydrochloric acid and aqueous saturated sodium chloride solution and then dried over Na2SO4. The solvent was evaporated in a vacuum and the residue was taken up in ether. The solid product was filtered off under suction and recrystallized from 2-propanol. There was obtained an isomer of the product, namely methyl 7-hydroxy-5-(trifluoromethyl)pyrazolo-[1,5-a]pyrimidine-3-carboxylate of m.p. 216°-217°. The product enriched in the mother liquors was crystallized from ethyl acetate. There was obtained methyl 5-hydroxy-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate of m.p. 149°-150°.

Workup

  1. temperaturewas heated to 100°
  2. temperatureAfter cooling to 20°
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with 1N aqueous hydrochloric acid and aqueous saturated sodium chloride solution
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated in a vacuum
  7. filtrationThe solid product was filtered off under suction
  8. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-a479e3a2abd64eb2a4bce52350040480
Source dataset
uspto-grants-1992_08
Patent number
US05138066

Reaction notes

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