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

HRID 474768Notes

Reaction equation

HRID 474768 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]3[NH:18][CH:19]=[C:20]([CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[N:29][CH:30]=4)[C:21](=[O:23])[N:22]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:31]([F:34])([F:33])[F:32].[CH3:35]CN(C(C)C)C(C)C.CI>ClC(Cl)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]3[N:18]([CH3:35])[CH:19]=[C:20]([CH2:24][C:25]4[CH:30]=[N:29][CH:28]=[N:27][CH:26]=4)[C:21](=[O:23])[N:22]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:31]([F:34])([F:32])[F:33]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178517736HCID 178517736, compound

Product 1

HCID 677757062-[2-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl]-1-methyl-5-(5-pyrimidinylmethyl)-4(1H)-pyrimidinoneYield 7.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To the solution of 2-[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl]-5-(5-pyrimidinylmethyl)-4(1H)-pyrimidinone (200 mg, 0.411 mmol) in dichloroethane (5 ml) was added DIPEA (0.143 ml, 0.822 mmol). It was stirred at rt for 30 min, mixed with MeI (0.031 ml, 0.493 mmol) dropwise, then stirred at r.t. overnight. Purification via MDAP then afforded the title compound (16 mg, 7.8%). LCMS: rt=3.04 min, [M+H+]=501

Workup

  1. stirringstirred at r.t. overnight
  2. customPurification via MDAP

Sources & evidence

ORD record
ord-54666e3b2971454e884d11d1a8c9860f
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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