Methyl iodide → 2-(3,5-difluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)phenethoxy)-5-ethyl-1-methylpyrimidin-4(1H)-one

HRID 474859Notes

Reaction equation

HRID 474859 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([F:31])[C:19]=1[O:20][C:21]1[CH:22]=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[N:25][CH:26]=1)[CH2:5][CH2:6][O:7][C:8]1[NH:9][CH:10]=[C:11]([CH2:15][CH3:16])[C:12](=[O:14])[N:13]=1.[CH3:32]CN(C(C)C)C(C)C.CI>C(Cl)Cl>[F:31][C:18]1[CH:17]=[C:4]([CH:3]=[C:2]([F:1])[C:19]=1[O:20][C:21]1[CH:26]=[N:25][C:24]([C:27]([F:29])([F:30])[F:28])=[N:23][CH:22]=1)[CH2:5][CH2:6][O:7][C:8]1[N:9]([CH3:32])[CH:10]=[C:11]([CH2:15][CH3:16])[C:12](=[O:14])[N:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178437203HCID 178437203, compound

Product 1

HCID 677752492-(3,5-difluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)phenethoxy)-5-ethyl-1-methylpyrimidin-4(1H)-oneYield 38.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 2-(3,5-difluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)phenethoxy)-5-ethylpyrimidin-4(1H)-one (30 mg, 0.068 mmol) and DIPEA (0.03 ml, 0.172 mmol) in DCM (1.5 ml) was added MeI (0.025 ml, 0.407 mmol). The solution was stirred at room temperature overnight. Purification via reverse phase flash chromatography then afforded the title compound (12 mg, 0.026 mmol, 38.8% yield). LCMS: rt=3.10 min, [M+H+]=457

Workup

  1. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-fbd59b6b417c44b0ab1ce1aac81d21ba
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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