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 706025Notes

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 mol, 6.0% yield). LCMS: rt=3.46 min, [M+H]=553

Workup

customPurification via MDAP

Sources & evidence

ORD record: ord-37df76becb5a44ce9899f33843a69fa2
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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