Sodium Iodide → (4-{[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-amino}-2-methyl-phenoxy)-acetic acid methyl ester

HRID 1242316Notes

Reaction equation

HRID 1242316 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH:19]2[CH2:21][CH2:20]2)=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:7][CH:8]=1.[CH3:22][O:23][C:24](=[O:36])[CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][CH3:34])=[CH:29][C:28]=1[CH3:35].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CS(C)=O.CCOCC>[CH3:22][O:23][C:24](=[O:36])[CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]([CH2:2][C:3]2[C:4]([CH:19]3[CH2:21][CH2:20]3)=[N:5][C:6]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=3)=[N:7][CH:8]=2)[CH3:34])=[CH:29][C:28]=1[CH3:35]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 219359605-Chloromethyl-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidineHCID 45097147Methyl [2-methyl-4-(methylamino)phenoxy]acetate

Product 1

HCID 67072224(4-{[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-amino}-2-methyl-phenoxy)-acetic acid methyl esterYield 64.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 400 mg (1.28 mmol) 5-chloromethyl-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine (example 27F]) and 268 mg (1.28 mmol) of (2-methyl-4-methylamino-phenoxy)-acetic acid methyl ester (example 5F]) in 8 ml of DMSO was added 194 mg (1.41 mmol) potasium carbonate and 192 mg (1.28 mmol) sodium iodide. The reaction mixture was stirred for 20 min at RT. It was then taken up in ether and washed with aqueous 10% KHSO4-solution (10%) and water. The crude product was purified by chromatography over silica gel with AcOEt/heptane 1:3, to give 403 mg of pure (4-{[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-amino}-2-methyl-phenoxy)-acetic acid methyl ester.

Workup

  1. washwashed with aqueous 10% KHSO4-solution (10%) and water
  2. customThe crude product was purified by chromatography over silica gel with AcOEt/heptane 1:3

Sources & evidence

ORD record
ord-a952df8a08c5490fafe1b7cc63321075
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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