Sodium Hydroxide → 2-(6-(2,4-dimethoxyphenyl)-4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)acetic acid

HRID 1056532

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[N:16]([CH2:17][C:18]([O:20]CC)=[O:19])[C:15](=[S:23])[NH:14][C:13](=[O:24])[CH:12]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[N:16]([CH2:17][C:18]([OH:20])=[O:19])[C:15](=[S:23])[NH:14][C:13](=[O:24])[CH:12]=1

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of ethyl 2-(6-(2,4-dimethoxyphenyl)-4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)acetate (6.8 g, 20.3 mmol) in methanol (34 mL) was added 6N aqueous NaOH (16.9 mL), and the solution was stirred at 35° C. for 3 hours. The mixture was concentrated under reduced pressure, and water (100 mL) was added. The aqueous layer was washed with ethyl acetate (2×200 mL), and acidified with concentrated HCl to pH˜2. The resultant acidic aqueous solution was extracted with EtOAc (3×200 mL), and the combined organic layers were dried with sodium sulfate, and concentrated under reduced pressure to give the title compound 6.53 g (99%) as a white solid.

Workup

concentrationThe mixture was concentrated under reduced pressure, and water (100 mL)
additionwas added
washThe aqueous layer was washed with ethyl acetate (2×200 mL)
extractionThe resultant acidic aqueous solution was extracted with EtOAc (3×200 mL)
dry with materialthe combined organic layers were dried with sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-34bea8c6f59a4f71ac8aa171e1f19abe
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399626B2

Linked notes

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