Potassium Carbonate → 2-{[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3,5-difluorophenyl)ethyl]oxy}-5-ethyl-4(1H)-pyrimidinone

HRID 474834Notes

Reaction equation

[C:1](=[NH:26])([O:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([C:21]([F:24])([F:23])[F:22])[CH:15]=2)=[C:8]([F:25])[CH:7]=1)[NH2:2].[CH2:27](/[C:29](=[CH:35]/O)/[C:30](OCC)=[O:31])[CH3:28].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][C:9]2[C:10]([F:12])=[CH:11][C:6]([CH2:5][CH2:4][O:3][C:1]3[NH:2][CH:35]=[C:29]([CH2:27][CH3:28])[C:30](=[O:31])[N:26]=3)=[CH:7][C:8]=2[F:25])=[CH:15][C:16]=1[C:21]([F:22])([F:24])[F:23]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3,5-difluorophenyl)ethyl imidocarbamate (250 mg, 0.459 mmol), ethyl (2Z)-2-ethyl-3-hydroxy-2-propenoate (132 mg, 0.918 mmol) and K2CO3 (127 mg, 0.918 mmol) in DMF (3 mL) was heated with a microwave condition at 110° C. for 1.5 h. Purification via MDAP afforded the title compound (60 mg, 27.5% yield). LCMS: rt=3.83 min, [M+H+]=475

Workup

customPurification via MDAP

Sources & evidence

ORD record: ord-8dbec3027a514eb1ad20351d07a78703
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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