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

HRID 474789Notes

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][C:27]4[CH:28]=[N:29][CH:30]=[N:31][CH:32]=4)[C:23](=[O:25])[N:24]=3)=[CH:11][C:10]=2[F:33])=[CH:4][C:3]=1[C:34]([F:37])([F:36])[F:35].[CH3:38]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]([CH3:38])[CH:21]=[C:22]([CH2:26][C:27]4[CH:32]=[N:31][CH:30]=[N:29][CH:28]=4)[C:23](=[O:25])[N:24]=3)=[CH:11][C:10]=2[F:33])=[CH:4][C:3]=1[C:34]([F:35])([F:36])[F:37]

Participants

Conditions

Temperature: 25 °C

Procedure

To the solution of 2-{[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3,5-difluorophenyl)ethyl]oxy}-5-(5-pyrimidinylmethyl)-4(1H)-pyrimidinone (80 mg, 0.148 mmol) and DIPEA (0.078 mL, 0.445 mmol) in DCM (3.0 mL) was added MeI (0.019 mL, 0.297 mmol) dropwise. The reaction mixture was stirred at room 25° C. for 3 h. Purification via MDAP then afforded the title compound (5 mg, 9.04 μmol, 6.0% yield). LCMS: rt=3.46 min, [M+H+]=553

Workup

customPurification via MDAP

Sources & evidence

ORD record: ord-4ed35aaca13d44af9bcddac9917b1831
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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