5-amino-1H-imidazole-4-carbonitrile → 4-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carbonitrile

HRID 225270

Reaction equation

HRID 225270 reaction equation
C[N:2]([CH3:17])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)=O.[NH2:18][C:19]1[N:20]=[CH:21][NH:22][C:23]=1C#N>C(O)(=O)C>[F:16][C:13]([F:14])([F:15])[C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:5]2[N:20]3[CH:21]=[N:22][C:23]([C:19]#[N:18])=[C:17]3[N:2]=[CH:3][CH:4]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 787775-amino-1H-imidazole-4-carbonitrileHCID 7300243-Dimethylamino-3'-trifluoromethylacrylophenone

Product 1

HCID 157125564-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.01 mole of 3-dimethylamino-3'-(trifluoromethyl)acrylophenone and 0.01 mole of 4-amino-5-imidazolecarbonitrile in 30 ml. of glacial acetic acid is refluxed for 6 hours. The solvent is removed under reduced pressure and worked up as for Example 29 to give the product as crystals, m.p. 168°-169° C.

Workup

  1. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-662297a6590c445487fb32c1e108f620
Source dataset
uspto-grants-1980_11
Patent number
US04236005

Linked notes

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