Trifluoroacetamidine → Ethyl 2,4-bis(trifluoromethyl)pyrimidine-5-carboxylate

HRID 2394271Notes

Reaction equation

HRID 2394271 reaction equation
C(O[CH:4]=[C:5]([C:11]([C:13]([F:16])([F:15])[F:14])=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[F:17][C:18]([F:23])([F:22])[C:19]([NH2:21])=[NH:20]>CCO>[CH2:9]([O:8][C:6]([C:5]1[C:11]([C:13]([F:14])([F:15])[F:16])=[N:20][C:19]([C:18]([F:23])([F:22])[F:17])=[N:21][CH:4]=1)=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 2776882TrifluoroacetamidineHCID 4685753Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate

Product 1

HCID 10493558Ethyl 2,4-bis(trifluoromethyl)pyrimidine-5-carboxylateYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl ethoxymethylene-4,4,4-trifluoroacetoacetate (15 g, 62.5 mmol) and trifluoroacetamidine (12.6 g, 112.5 mmol) in EtOH (50 mL) was heated at reflux for 24 h under N2. The reaction mixture was cooled and concentrated. Chromatography (SiO2, 20% EtOAc/hexane) afforded ethyl-2,4-bis (trifluoromethyl)pyrimidine-5-carboxylate as an oil (7.0 g, 39%), 1HNMR (CDCl3) δ 9.37 (s, 1H), 3.70 (q, 2H), 1.27 (t, 3H).

Workup

  1. temperatureat reflux for 24 h under N2
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4baead46329c48d7a417b6270e76d3e4
Source dataset
uspto-grants-1998_09
Patent number
US05811428

Reaction notes

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