Ethyl Acetate → [5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid 2-cyclohexyloxy-ethyl ester

HRID 348469Notes

Reaction equation

HRID 348469 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]([O:17][CH2:18][C:19]([OH:21])=[O:20])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[CH:22]1([O:28][CH2:29][CH2:30]O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(OCC)(=O)C>ClCCl>[CH:22]1([O:28][CH2:29][CH2:30][O:20][C:19](=[O:21])[CH2:18][O:17][C:14]2[N:13]=[CH:12][C:11]([C:9](=[O:10])[NH:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:16][N:15]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2247752-(Cyclohexyloxy)ethanolHCID 21087356[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid

Product 1

HCID 69523264[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid 2-cyclohexyloxy-ethyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The titled compound was prepared from [5-(4-fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid using 2-cyclohexyloxy-ethanol (37 mg, 0.26 mmol) as the coupling partner. Chromatography (1:1 ethyl acetate:dichloromethane) through SiO2 yielded 36 mg (51%) of the titled compound. ESI-MS m/z 418 (MH30 ), 416 (M−H−).

Sources & evidence

ORD record
ord-00afb08231c04ebfbbf49e3c84463202
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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