Methanol → [5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid cyclobutylmethyl ester

HRID 348462Notes

Reaction equation

HRID 348462 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([CH2:26]O)[CH2:25][CH2:24][CH2:23]1.CO>ClCCl>[CH:22]1([CH2:26][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)[CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 887MethanolHCID 78130CyclobutylcarbinolHCID 21087356[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid

Product 1

HCID 69522798[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid cyclobutylmethyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The titled compound was prepared from [5-(4-fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid using cyclobutanemethanol (32 μL, 0.34 mmol) as the coupling partner. Chromatography (1:1 methanol:dichloromethane) through SiO2 yielded 56 mg (92%) of the titled compound. ESI-MS m/z 360 (MH+), 358 (M−H−).

Sources & evidence

ORD record
ord-b6a206b14c174480a9062e2b98f133d9
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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