Potassium Carbonate → 2-{[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3,5-difluorophenyl)ethyl]oxy}-5-{[2-(methyloxy)-5-pyrimidinyl]methyl}-4(1H)-pyrimidinone

HRID 706090Notes

Reaction equation

HRID 706090 reaction equation
[C:1](=[NH:26])([O:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([C:21]([F:24])([F:23])[F:22])[CH:15]=2)=[C:8]([F:25])[CH:7]=1)[NH2:2].[OH:27]/[CH:28]=[C:29](/[CH2:35][C:36]1[CH:37]=[N:38][C:39]([O:42][CH3:43])=[N:40][CH:41]=1)\[C:30](OCC)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][C:9]2[C:10]([F:12])=[CH:11][C:6]([CH2:5][CH2:4][O:3][C:1]3[NH:2][CH:30]=[C:29]([CH2:35][C:36]4[CH:37]=[N:38][C:39]([O:42][CH3:43])=[N:40][CH:41]=4)[C:28](=[O:27])[N:26]=3)=[CH:7][C:8]=2[F:25])=[CH:15][C:16]=1[C:21]([F:22])([F:24])[F:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 866661972-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-3,5-difluorophenyl)ethyl imidocarbamateHCID 86666245ethyl(2Z)-3-hydroxy-2-{[2-(methyloxy)-5-pyrimidinyl]methyl}-2-propenoate

Product 1

HCID 1784941522-{[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3,5-difluorophenyl)ethyl]oxy}-5-{[2-(methyloxy)-5-pyrimidinyl]methyl}-4(1H)-pyrimidinoneYield 15.04%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The same procedure as E125 from 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3,5-difluorophenyl)ethyl imidocarbamate (143 mg, 0.362 mmol), ethyl (2Z)-3-hydroxy-2-{[2-(methyloxy)-5-pyrimidinyl]methyl}-2-propenoate (129 mg, 0.543 mmol) and K2CO3 (125 mg, 0.906 mmol) in DMF (3 mL), except that the reaction temperature was 130° C., to afford the title compound (31 mg, 0.054 mmol, 15.04% yield) as white solid. LCMS: rt=3.61 min, [M+H+]=569

Workup

  1. customwas 130° C.

Sources & evidence

ORD record
ord-028e6a414ad94088aac3c6abdc7027f4
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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