Ammonia → N-[3-fluoro-4-(trifluoromethyl)phenyl]-5-methyl-2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

HRID 591230Notes

Reaction equation

HRID 591230 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.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[C:17]([F:25])[CH:16]=1.N>C(O)C>[F:25][C:17]1[CH:16]=[C:15]([NH:14][C:2]2[N:7]3[N:8]=[C:9]([S:11][CH3:12])[N:10]=[C:6]3[N:5]=[C:4]([CH3:13])[CH:3]=2)[CH:20]=[CH:19][C:18]=1[C:21]([F:23])([F:24])[F:22]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 27359144-Amino-2-fluorobenzotrifluorideHCID 105128437-Chloro-5-methyl-2-(methylthio)-[1,2,4]triazolo[1,5-a]pyrimidine2×

Product 1

HCID 67119856N-[3-fluoro-4-(trifluoromethyl)phenyl]-5-methyl-2-(methylthio)[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 (0.3 g, 1.397 mmol)) in ethanol (5 mL), 4-amino-2-fluorobenzotrifluoride (ALFAAESAR, 0.25 g, 1.397 mmol) was added and the mixture was stirred at room temperature for 2 h. Anhydrous ammonia (0.2 mL, 1.397 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-b206af13d4e24b5997e2449ad34b5adc
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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