Diisopropylethylamine → (3,5-Bis-trifluoromethyl-benzyl)-(5-bromopyrimidin-2-yl)-amine

HRID 604201Notes

Reaction equation

HRID 604201 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH2:6][NH2:7].[Br:17][C:18]1[CH:19]=[N:20][C:21](Cl)=[N:22][CH:23]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:12])[F:13])[CH:10]=1)[CH2:6][NH:7][C:21]1[N:22]=[CH:23][C:18]([Br:17])=[CH:19][N:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 57551007(3,5-Bis-trifluoromethyl-benzyl)-(5-bromopyrimidin-2-yl)-amineYield 61.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3,5-Bis-trifluoromethyl-benzylamine (10 g) and 5-bromo-2-chloro-pyrimidine (12 g) are dissolved in 1,4-dioxane (50 ml) and thereto is added N,N-diisopropylethylamine (10.7 ml) and the mixture is heated under reflux overnight. The reaction solution is cooled to room temperature and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3) to give (3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amine (10.1 g). MS (m/z): 713 [M+H]+

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3)

Sources & evidence

ORD record
ord-c48a0666e4c64d7883a72b154c487c76
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

Loading…