Methanol → 4-(2,5-dimethylpyrimidin-4-yl)-1-methyl-1H-pyrazole-5-carboxylic acid

HRID 874357Notes

Reaction equation

[OH-].[Na+].CO.[CH3:5][C:6]1[N:11]=[C:10]([C:12]2[CH:13]=[N:14][N:15]([CH3:21])[C:16]=2[C:17]([O:19]C)=[O:18])[C:9]([CH3:22])=[CH:8][N:7]=1>O>[CH3:5][C:6]1[N:11]=[C:10]([C:12]2[CH:13]=[N:14][N:15]([CH3:21])[C:16]=2[C:17]([OH:19])=[O:18])[C:9]([CH3:22])=[CH:8][N:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium hydroxide (0.31 g) was added to a mixed solution of methanol (15 ml) and water (15 ml) containing the methyl 4-(2,5-dimethylpyrimidin-4-yl)-1-methyl-1H-pyrazole-5-carboxylate (1.9 g) obtained in (Example 3.22) <Step 1>, and the obtained mixture was then stirred at 50° C. for 1 hour. Thereafter, methanol was distilled away from the reaction solution under reduced pressure, and the residue was then adjusted to pH 5-6 by addition of 1 N hydrochloric acid. Thereafter, water was distilled away under reduced pressure. The obtained residue was washed with methylene chloride, and the filtrate was then concentrated under reduced pressure, so as to obtain the title compound (0.94 g) in the form of a yellow solid.

Workup

customobtained in (Example 3.22) <Step 1>
distillationThereafter, methanol was distilled away from the reaction solution under reduced pressure
additionthe residue was then adjusted to pH 5-6 by addition of 1 N hydrochloric acid
distillationThereafter, water was distilled away under reduced pressure
washThe obtained residue was washed with methylene chloride
concentrationthe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record: ord-886331624abc4c2d823e3de60c6b6614
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980888B2

Reaction notes

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