Ammonia → 2-(1,1-Difluoroethyl)-5-Methyl-N-[4-(Trifluoromethyl)phenyl][1,2,4]triazolo[1,5-A]pyrimidin-7-Amine

HRID 591249Notes

Reaction equation

HRID 591249 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:11]([F:14])([F:13])[CH3:12])[N:10]=[C:6]2[N:5]=[C:4]([CH3:15])[CH:3]=1.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.N.CO>C(O)C>[F:13][C:11]([C:9]1[N:10]=[C:6]2[N:5]=[C:4]([CH3:15])[CH:3]=[C:2]([NH:22][C:21]3[CH:23]=[CH:24][C:18]([C:17]([F:16])([F:25])[F:26])=[CH:19][CH:20]=3)[N:7]2[N:8]=1)([F:14])[CH3:12]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 99644-(Trifluoromethyl)anilineHCID 533918697-Chloro-2-(1,1-difluoroethyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 513492762-(1,1-Difluoroethyl)-5-Methyl-N-[4-(Trifluoromethyl)phenyl][1,2,4]triazolo[1,5-A]pyrimidin-7-Amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of Intermediate 3 (10 g, 43 mmol) in ethanol (150 mL), 4-(trifluoromethyl)aniline (ALDRICH, 6.93 g, 43 mmol) was added and the mixture was stirred at room temperature for 1 h. 7M Ammonia in MeOH (6.14 mL, 43 mmol) was added to neutralize the hydrochloride salt and solvent was removed in vacuo. The crude mixture was purified by flash chromatography (Si, eluting with Hexane/EtOAc mixtures from 95:5 to 40:60%) to yield the title compound as a yellow solid.

Workup

  1. additionwas added
  2. customwas removed in vacuo
  3. customThe crude mixture was purified by flash chromatography (Si, eluting with Hexane/EtOAc mixtures from 95:5 to 40:60%)

Sources & evidence

ORD record
ord-24085c760348451585cc2efb4b8695b9
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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