Methyl iodide → HCID 86666241, compound

HRID 474835Notes

Reaction equation

HRID 474835 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][C:7]2[CH:27]=[CH:26][C:10]([CH2:11][CH2:12][O:13][C:14]3[NH:15][CH:16]=[C:17]([CH2:21][C:22]([F:25])([F:24])[F:23])[C:18](=[O:20])[N:19]=3)=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:30]([F:33])([F:32])[F:31].[CH3:34]CN(C(C)C)C(C)C.CI>C(Cl)Cl>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][C:7]2[CH:27]=[CH:26][C:10]([CH2:11][CH2:12][O:13][C:14]3[N:15]([CH3:34])[CH:16]=[C:17]([CH2:21][C:22]([F:25])([F:24])[F:23])[C:18](=[O:20])[N:19]=3)=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:30]([F:31])([F:33])[F:32]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178518459HCID 178518459, compound

Product 1

HCID 86666241HCID 86666241, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(4-chloro-3-(trifluoromethyl)phenoxy)phenethoxy)-5-(2,2,2-trifluoroethyl)pyrimidin-4(1H)-one (66 mg, 0.134 mmol) in DCM (10 mL) was added DIPEA (0.070 mL, 0.402 mmol) and MeI (0.013 mL, 0.201 mmol). The mixture was stirred at room temperature for 3 h. Purification via reverse phase flash chromatography then afforded the title compound (28 mg, 41.3% yield). LCMS: rt=3.73 min, [M+H+]=507

Workup

  1. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-497ebce980004cd9b844148bcdab6232
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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