Methyl iodide → HCID 67775665, compound

HRID 706043Notes

Reaction equation

HRID 706043 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][S:18][C:19]3[NH:20][CH:21]=[C:22]([CH2:26][CH3:27])[C:23](=[O:25])[N:24]=3)=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:28]([F:31])([F:30])[F:29].[CH3:32]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[CH:16]=[CH:15][C:14]([CH2:17][S:18][C:19]3[N:20]([CH3:32])[CH:21]=[C:22]([CH2:26][CH3:27])[C:23](=[O:25])[N:24]=3)=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:28]([F:30])([F:29])[F:31]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178437208HCID 178437208, compound

Product 1

HCID 67775665HCID 67775665, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-{[(5-ethyl-4-oxo-1,4-dihydro-2-pyrimidinyl)thio]methyl}benzonitrile (120 mg, 0.258 mmol) and DIPEA (0.090 ml, 0.515 mmol) in DCM (2 mL) was added MeI (0.02416 ml, 0.386 mmol). The mixture was stirred at room temperature for 2 h. The reaction was then quenched with water, extracted with EA. The combined organic layers were dried with Na2SO4, filtered, concentrated and purified via reverse phase flash chromatography to afford the title compound (40 mg, 32.4% yield). LCMS: rt=3.44 min, [M+H+]=480

Workup

  1. customThe reaction was then quenched with water
  2. extractionextracted with EA
  3. dry with materialThe combined organic layers were dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified via reverse phase flash chromatography

Sources & evidence

ORD record
ord-35de367426304a7daa54133320beff1b
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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