Methanol → (2E)-3-[4-(1-cyclohexyl-3-methyl-7-oxo-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-3-methoxyphenyl]-2-propenic acid

HRID 915980Notes

Reaction equation

HRID 915980 reaction equation
CO.[CH:3]1([N:9]2[C:17]3[C:16](=[O:18])[NH:15][C:14]([C:19]4[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27]([O:29]C)=[O:28])=[CH:21][C:20]=4[O:31][CH3:32])=[N:13][C:12]=3[C:11]([CH3:33])=[N:10]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[OH-].[Na+]>O>[CH:3]1([N:9]2[C:17]3[C:16](=[O:18])[NH:15][C:14]([C:19]4[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])=[CH:21][C:20]=4[O:31][CH3:32])=[N:13][C:12]=3[C:11]([CH3:33])=[N:10]2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 136005762Methyl (2E)-3-[4-(1-cyclohexyl-3-methyl-7-oxo-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-3-methoxyphenyl]-2-propenate

Product 1

HCID 136005776(2E)-3-[4-(1-cyclohexyl-3-methyl-7-oxo-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-3-methoxyphenyl]-2-propenic acidYield 89.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 1 ml methanol suspension of 45 mg (0.107 mmol) of the compound obtained in Example 226, 1 ml of a 1M aqueous solution of sodium hydroxide was added, and the mixture was stirred at room temperature for 2 hours. Then, the reaction mixture was diluted with water, and the aqueous layer was washed with ether. The aqueous layer was acidified with a 2M aqueous solution of hydrochloric acid, and precipitated solids were collected by filtration to obtain 39 mg (89%) of the captioned compound.

Workup

  1. additionwas added
  2. washthe aqueous layer was washed with ether
  3. customprecipitated solids
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-78f60c437ec6495aba51623f0fb1e8c0
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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