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

HRID 706022Notes

Reaction equation

[CH2:1](/[C:3](=[CH:9]/O)/[C:4](OCC)=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].[C:17](=[NH:40])([O:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([C:36]([F:39])([F:38])[F:37])[CH:30]=2)=[CH:24][CH:23]=1)[NH2:18]>CN1C(=O)CCC1>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([O:28][C:25]2[CH:24]=[CH:23][C:22]([CH2:21][CH2:20][O:19][C:17]3[NH:18][CH:9]=[C:3]([CH2:1][CH3:2])[C:4](=[O:5])[N:40]=3)=[CH:27][CH:26]=2)=[CH:30][C:31]=1[C:36]([F:39])([F:38])[F:37]

Participants

Conditions

Temperature: 160 °C

Procedure

To the suspension of ethyl (2Z)-2-ethyl-3-hydroxy-2-propenoate (281 mg, 1.951 mmol) and K2CO3 (270 mg, 1.951 mmol) in NMP (10 mL) was added 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl imidocarbamate (350 mg, 0.976 mmol). The reaction mixture was heated with a microwave reactor at 160° C. for 1.5 h. Purification via MDAP then afforded the title compound (165 mg, 38.5% yield). LCMS: rt=3.89 min, [M+H+]=439

Workup

customPurification via MDAP

Sources & evidence

ORD record: ord-6324fc38ac2547c686649212a6575d5e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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