Water → 5-bromo-6-(2,4,6-trifluorophenyl)-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine

HRID 1786297Notes

Reaction equation

HRID 1786297 reaction equation
[Br:1][C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([F:15])=[CH:10][C:9]=2[F:16])=[C:6](Br)[N:5]2[N:18]=[CH:19][N:20]=[C:4]2[N:3]=1.Cl.[F:22][C:23]([F:28])([F:27])[C@@H:24]([NH2:26])[CH3:25].C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[Br:1][C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([F:15])=[CH:10][C:9]=2[F:16])=[C:6]([NH:26][C@@H:24]([CH3:25])[C:23]([F:28])([F:27])[F:22])[N:5]2[N:18]=[CH:19][N:20]=[C:4]2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 130939192-Propanamine, 1,1,1-trifluoro-, hydrochloride (1:1), (2S)-HCID 161030265,7-Dibromo-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 161030295-bromo-6-(2,4,6-trifluorophenyl)-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amineYield 17.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5,7-dibromo-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine (320 mg, 0.78 mmol), (1S)-2,2,2-trifluoro-1-methylethylamine hydrogen chloride (235 mg, 1.57 mmol), and diisopropylethylamine (260 mg, 2.0 mmol) in 5 mL of N,N-dimethylformamide is stirred at room temperature for 18 h. Water is added to quench the reaction, and the product is extracted with ethyl acetate. The combined organic extracts are washed with saturated sodium chloride (x3), dried over magnesium sulfate, and concentrated to a residue. The residue is chromatographed over silica gel, eluting with a gradient of 9:1 hexanes/ethyl acetate to 2:1 hexanes/ethyl acetate. Concentration provides 5-bromo-6-(2,4,6-trifluorophenyl)-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine as a light tan solid (60 mg, mp 95-97° C.). MS: m/z 440.0, 442.0 (M+H).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe product is extracted with ethyl acetate
  4. washThe combined organic extracts are washed with saturated sodium chloride (x3)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to a residue
  7. customThe residue is chromatographed over silica gel
  8. washeluting with a gradient of 9:1 hexanes/ethyl acetate to 2:1 hexanes/ethyl acetate
  9. concentrationConcentration

Sources & evidence

ORD record
ord-c47997c64243437f9f2f3d828ae764c4
Source dataset
uspto-grants-2009_03
Patent number
US07507739B2

Reaction notes

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