Diisopropylethylamine → (4-Chloro-5-trifluoromethyl-pyrimidin-2-yl)-(2-trifluoromethoxy-benzyl)-amine

HRID 1819409Notes

Reaction equation

HRID 1819409 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[C:4]([Cl:10])=[N:5][C:6](Cl)=[N:7][CH:8]=1.[F:13][C:14]([F:25])([F:24])[O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19].CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:10][C:4]1[C:3]([C:2]([F:12])([F:11])[F:1])=[CH:8][N:7]=[C:6]([NH:19][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[O:15][C:14]([F:13])([F:24])[F:25])[N:5]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2777251(2-(Trifluoromethoxy)phenyl)methanamineHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidine

Product 1

HCID 57885586(4-Chloro-5-trifluoromethyl-pyrimidin-2-yl)-(2-trifluoromethoxy-benzyl)-amineYield 52%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(trifluoromethyl)-2,4-di-chloropyrimidine (0.5 g, 2.3 mmol) in DMF (8 mL) were added a solution of 2-(trifluoromethoxy)benzylamine (0.44g, 2.3 mmol) in DMF (2 mL) followed by DIPEA (0.44 mL, 2.3 mmol) at −20° C. The reaction mixture was stirred at that temperature for 20 min. When the starting material was all consumed, the mixture was diluted with EtOAc and washed with water (×4). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified by silica gel preparative TLC using 100% CH2Cl2 as an eluent to afford 0.44 g (52%) of (4-chloro-5-trifluoromethyl-pyrimidin-2-yl)-(2-trifluoromethoxy-benzyl)-amine as a white foam.

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-a92784974984469198b2c54208545eb9
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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