4-chloro-3-(6-methyl-2-oxo-4-trifluoromethyl-2H-pyrimidin-1-yl)-benzoic acid ethyl ester → 4-chloro-3-(6-methyl-2-oxo-4-trifluoromethyl-2H-pyrimidin-1-yl)-benzoic acid

HRID 661667Notes

Reaction equation

C([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([N:12]2[C:17]([CH3:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[N:14][C:13]2=[O:23])[CH:6]=1)C>Cl>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:24])=[O:3])=[CH:6][C:7]=1[N:12]1[C:17]([CH3:18])=[CH:16][C:15]([C:19]([F:20])([F:21])[F:22])=[N:14][C:13]1=[O:23]

Participants

Conditions

Temperature: 85 °C

Procedure

A stirred suspension of 4-chloro-3-(6-methyl-2-oxo-4-trifluoromethyl-2H-pyrimidin-1-yl)-benzoic acid ethyl ester (3.34 g, 9.26 mmol) in 12N aq. HCl solution (10 mL) was heated at 85° C. for 1 h. After cooling to room temperature the organics were extracted into DCM (3×100 mL). The combined organic layer was dried over MgSO4 and filtered. Concentration in vacuo gave a yellow solid which was purified via silica gel flash chromatography (eluting with a gradient of 5% to 10% MeOH in DCM, followed by 9% MeOH and 1% AcOH in DCM) to give 4-chloro-3-(6-methyl-2-oxo-4-trifluoromethyl-2H-pyrimidin-1-yl)-benzoic acid (1.0 g, 33%) as a cream solid. MS (M+H)+: 332.8, tR=2.364 min (method 1); 1H NMR (CDCl3) δ 8.17 (1H, dd, J=8.4, 2.4 Hz), 8.04 (1H, d, J=1.5 Hz), 7.72 (1H, d, J=8.4 Hz), 6.72 (1H, s), 2.17 (3H, s).

Workup

temperatureAfter cooling to room temperature the
extractionorganics were extracted into DCM (3×100 mL)
dry with materialThe combined organic layer was dried over MgSO4
filtrationfiltered
concentrationConcentration in vacuo
customgave a yellow solid which
customwas purified via silica gel flash chromatography (
washeluting with a gradient of 5% to 10% MeOH in DCM

Sources & evidence

ORD record: ord-366b81b055a74f3d9fc109b0872005fa
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084614B2

Reaction notes

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