Potassium Carbonate → HCID 178513405, compound

HRID 1801746Notes

Reaction equation

HRID 1801746 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[N:8]2[CH:9]=[N:10][C:11]([C:12]#[N:13])=[C:7]2[N:6]=[C:5]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:4]=1.Cl.[NH2:27][OH:28].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:28][NH:27][C:12]([C:11]1[N:10]=[CH:9][N:8]2[C:3]([C:2]([F:24])([F:1])[F:25])=[CH:4][C:5]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=3)=[N:6][C:7]=12)=[NH:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 11164124HCID 11164124, compound

Product 1

HCID 178513405HCID 178513405, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carbonitrile [CAS-No. 851263-42-8] 1.16 g, 3.26 mmol), hydroxylamine hydrochloride (0.46 g, 6.62 mmol) and potassium carbonate (1.35 g, 9.77 mmol) in ethanol (50 ml) was heated under reflux conditions for 3 h. The precipitate was collected by filtration and washed with ethanol, the combined filtrates were evaporated and the crude product purified by column chromatography on silica gel (ethyl acetate/ethanol 95:5) and crystallization from diethyl ether/hexane to yield the title compound (257 mg, 20%) as a red solid. MS (ISN) 388.2 [(M−H)−]; mp 213° C.

Workup

  1. temperaturewas heated under reflux conditions for 3 h
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with ethanol
  4. customthe combined filtrates were evaporated
  5. customthe crude product purified by column chromatography on silica gel (ethyl acetate/ethanol 95:5) and crystallization from diethyl ether/hexane

Sources & evidence

ORD record
ord-4ee3f9fff50c4c698944464f5fa5f636
Source dataset
uspto-grants-2013_01
Patent number
US08349844B2

Reaction notes

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