4-(Trifluoromethyl)aniline → 2-cyclopropyl-5-methyl-N-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine

HRID 591246Notes

Reaction equation

HRID 591246 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH:11]3[CH2:13][CH2:12]3)[N:10]=[C:6]2[N:5]=[C:4]([CH3:14])[CH:3]=1.[F:15][C:16]([F:25])([F:24])[C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>C(O)C>[CH:11]1([C:9]2[N:10]=[C:6]3[N:5]=[C:4]([CH3:14])[CH:3]=[C:2]([NH:21][C:20]4[CH:22]=[CH:23][C:17]([C:16]([F:15])([F:24])[F:25])=[CH:18][CH:19]=4)[N:7]3[N:8]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 533918677-Chloro-2-cyclopropyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 513476922-cyclopropyl-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 20 (0.04 g, 0.192 mmol) in ethanol (2.5 mL), 4-(trifluoromethyl)aniline (ALDRICH, 0.031 g, 0.192 mmol) was added and the mixture was stirred under reflux for 2 h. Solvent was removed in vacuo and the crude mixture was purified by preparative HPLC (SunFire 19×150 mm, H2O 0.1% TFA-ACN 0.1% TFA gradient from 10 to 100%) to yield a beige solid which was further purified by preparative HPLC (SunFire 19×150 mm, H2O 0.1% TFA-ACN 0.1% TFA gradient from 30 to 100%) to yield the title compound as a white solid.

Workup

  1. additionwas added
  2. temperatureunder reflux for 2 h
  3. customSolvent was removed in vacuo
  4. customthe crude mixture was purified by preparative HPLC (SunFire 19×150 mm, H2O 0.1% TFA-ACN 0.1% TFA gradient from 10 to 100%)
  5. customto yield a beige solid which
  6. customwas further purified by preparative HPLC (SunFire 19×150 mm, H2O 0.1% TFA-ACN 0.1% TFA gradient from 30 to 100%)

Sources & evidence

ORD record
ord-ba542758aeb14b25b8fe781be81e07bc
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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