3-Dimethylamino-3'-trifluoromethylacrylophenone → Ethyl 4-(alpha,alpha,alpha-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxylate

HRID 225277Notes

Reaction equation

HRID 225277 reaction equation
[NH2:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].CN(C)[CH:14]=[CH:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1)=O>C(O)(=O)C>[F:25][C:24]([F:26])([F:27])[C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:16]2[N:6]3[CH:5]=[N:4][C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]3[N:1]=[CH:14][CH:15]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 7300243-Dimethylamino-3'-trifluoromethylacrylophenoneHCID 178470302HCID 178470302, compound

Product 1

HCID 23329853Ethyl 4-(alpha,alpha,alpha-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.55 g. of ethyl 5-aminoimidazole-4-carboxylate and 2.43 g. of 3-dimethylamino-3'-trifluoromethylacrylophenone in 25 ml. of glacial acetic acid is refluxed for 6 hours. On cooling the product crystallized from solution, m.p. 232°-234° C.

Workup

  1. additionA mixture of 1.55 g
  2. temperatureOn cooling the product
  3. customcrystallized from solution, m.p. 232°-234° C.

Sources & evidence

ORD record
ord-c5d3e9d47c354eed9d8cd1c19bf8ab1d
Source dataset
uspto-grants-1980_11
Patent number
US04236005

Reaction notes

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