Methyl iodide → 2-{[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3,5-difluorophenyl)ethyl]oxy}-5-ethyl-1-methyl-4(1H)-pyrimidinone

HRID 706089Notes

Reaction equation

HRID 706089 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([CH2:16][CH2:17][O:18][C:19]3[NH:20][CH:21]=[C:22]([CH2:26][CH3:27])[C:23](=[O:25])[N:24]=3)=[CH:11][C:10]=2[F:28])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].[CH3:33]CN(C(C)C)C(C)C.CI>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([CH2:16][CH2:17][O:18][C:19]3[N:20]([CH3:33])[CH:21]=[C:22]([CH2:26][CH3:27])[C:23](=[O:25])[N:24]=3)=[CH:11][C:10]=2[F:28])=[CH:4][C:3]=1[C:29]([F:31])([F:32])[F:30]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 1784372022-{[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3,5-difluorophenyl)ethyl]oxy}-5-ethyl-4(1H)-pyrimidinone

Product 1

HCID 866662432-{[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3,5-difluorophenyl)ethyl]oxy}-5-ethyl-1-methyl-4(1H)-pyrimidinoneYield 14.44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The same procedure as E141 from 2-{[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3,5-difluorophenyl)ethyl]oxy}-5-ethyl-4(1H)-pyrimidinone (60 mg, 0.126 mmol), DIPEA (0.044 mL, 0.253 mmol) and MeI (0.012 mL, 0.190 mmol) in DCM (2 mL), except that the reaction time was 3 h, to afford the title compound (11 mg, 0.018 mmol, 14.44% yield). LCMS: rt=3.62 min, [M+H+]=489

Sources & evidence

ORD record
ord-a52e98f4241b487b92c01810d74a268a
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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