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

HRID 591231Notes

Reaction equation

HRID 591231 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([S:11][CH3:12])[N:10]=[C:6]2[N:5]=[C:4]([CH3:13])[CH:3]=1.[F:14][C:15]([F:24])([F:23])[C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.N>C(O)C>[CH3:13][C:4]1[CH:3]=[C:2]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([C:15]([F:14])([F:23])[F:24])=[CH:17][CH:18]=2)[N:7]2[N:8]=[C:9]([S:11][CH3:12])[N:10]=[C:6]2[N:5]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 99644-(Trifluoromethyl)anilineHCID 105128437-Chloro-5-methyl-2-(methylthio)-[1,2,4]triazolo[1,5-a]pyrimidine2×

Product 1

HCID 513476945-methyl-2-(methylthio)-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 7-chloro-5-methyl-2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidine (Intermediate 8 (0.2 g, 0.932 mmol) in ethanol (5 mL), 4-(trifluoromethyl)aniline (ALDRICH, 0.117 mL, 0.932 mmol) was added and the mixture was stirred at room temperature for 3 h. Anhydrous ammonia (0.133 mL, 0.932 mmol) was added and solvent was removed in vacuo. The residue was purified by flash chromatography (Si, eluting with Hexane/EtOAc mixtures form 95:5 to 40:60%) to yield the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-8dc5473516ef441a9ad958a4c0ad5bb5
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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