Dichloromethane → 2-(4-Benzyloxycarbonyl-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine

HRID 2112089Notes

Reaction equation

HRID 2112089 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:19][C:20]1[CH:35]=[CH:34][C:23]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])=[CH:22][C:21]=1[O:36][CH3:37].ClCCl>O1CCOCC1.CO>[CH2:27]([O:26][C:24]([C:23]1[CH:34]=[CH:35][C:20]([NH:19][C:2]2[N:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=2)=[C:21]([O:36][CH3:37])[CH:22]=1)=[O:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 58200992Benzyl 4-amino-3-methoxybenzoate

Product 1

HCID 582010032-(4-Benzyloxycarbonyl-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

2 g (9.217 mmol) 2,4-dichloro-5-trifluoromethylpyrimidine are dissolved in 4 ml dioxane and combined with 6.01 g (18.430 mmol) caesium carbonate and 2.16 g (7.363 mmol) benzyl 4-amino-3-methoxybenzoate (WO 9825901). This suspension is stirred for 30 h at 100° C. The suspension is combined with 50 ml dichloromethane and methanol and filtered to remove the insoluble constituents. The solvent is eliminated in vacuo and the residue is purified by column chromatography. The carrier used is silica gel and the eluant used is a mixture of 85% cyclohexane and 15% ethyl acetate.

Workup

  1. filtrationfiltered
  2. customto remove the insoluble constituents
  3. customthe residue is purified by column chromatography
  4. additiona mixture of 85% cyclohexane and 15% ethyl acetate

Sources & evidence

ORD record
ord-b0ba5619ff7a44cb9ca78a5b0d85d373
Source dataset
uspto-grants-2009_04
Patent number
US07521457B2

Reaction notes

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