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

HRID 591250Notes

Reaction equation

HRID 591250 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]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[C:24]([F:27])([F:26])[F:25])[NH2:20]>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:20][C:19]3[CH:21]=[CH:22][C:23]([C:24]([F:25])([F:26])[F:27])=[C:17]([F:16])[CH:18]=3)[N:7]2[N:8]=1)([F:14])[CH3:12]

Participants

4

Reactant 2

HCID 27359144-Amino-2-fluorobenzotrifluorideHCID 533918697-Chloro-2-(1,1-difluoroethyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 513475442-(1,1-difluoroethyl)-N-[3-fluoro-4-(trifluoromethyl)phenyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of Intermediate 3 (0.1 g, 0.43 mmol) and 3-fluoro-4-(trifluoromethyl)aniline (ALFAAESAR, 0.077 g, 0.43 mmol) in ethanol (5 mL) was heated at 50° C. for 1 h. The reaction mixture was concentrated under vacuum, redissolved in DCM (20 mL) and washed with aq. Na2CO3 (2×15 mL). The organic layer was dried over anhydrous Na2SO4 filtered and concentrated under vacuum to afford a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionredissolved in DCM (20 mL)
  3. washwashed with aq. Na2CO3 (2×15 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto afford a white solid

Sources & evidence

ORD record
ord-61e402e36509418788d37515fa7c7991
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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