Water → 1-[2-(Trifluoromethyl)pyrimidin-5-yl]methanamine

HRID 1181438Notes

Reaction equation

HRID 1181438 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[N:7][C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:6]=[N:7][C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 858698555-Azidomethyl-2-(trifluoromethyl)pyrimidine

Product 1

HCID 450733911-[2-(Trifluoromethyl)pyrimidin-5-yl]methanamineYield 55.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(azidomethyl)-2-(trifluoromethyl)pyrimidine (Description 120; 660 mg, 3.26 mmol) in anhydrous THF (10 ml) was added triphenylphosphine (1.71 g, 6.52 mmol) and water (0.059 ml, 3.26 mmol) and the resulting mixture stirred at room temperature overnight. The mixture was evaporated and the residue purified by column chromatography on silica elution with 5% MeOH in DCM+0.5% NH4OH to give the title compound (320 mg, 55%) as a pale yellow solid.

Workup

  1. customThe mixture was evaporated
  2. customthe residue purified by column chromatography on silica elution with 5% MeOH in DCM+0.5% NH4OH

Sources & evidence

ORD record
ord-64469a26665d4d448894d148df3eac04
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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