Water → HCID 69747030, compound

HRID 2181350Notes

Reaction equation

HRID 2181350 reaction equation
O.[OH-].[Li+].O.[CH3:5][N:6]1[C:11](=[O:12])[C:10]2[C:13]([CH:27]=[CH:28][C:29]([O:31]C)=[O:30])=[C:14]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([F:26])([F:25])[F:24])[S:15][C:9]=2[N:8]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:7]1=[O:37]>O1CCCC1>[CH3:5][N:6]1[C:11](=[O:12])[C:10]2[C:13]([CH:27]=[CH:28][C:29]([OH:31])=[O:30])=[C:14]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([F:26])([F:24])[F:25])[S:15][C:9]=2[N:8]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:7]1=[O:37]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86592984HCID 86592984, compound

Product 1

HCID 69747030HCID 69747030, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (0.20 g) and water (6 ml) were added to a solution of 3-[1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidin-5-yl]-2-propenoic acid, methyl ester (0.20 g) in tetrahydrofuran (7 ml) and stirred at room temperature for 20 hours. The solution was neutralised to pH7 and extracted with dichloromethane. The organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash silica chromatography eluting with a gradient of 0-5% ethanol in dichloromethane to give the title compound as a white solid (0.10 g).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash silica chromatography
  6. washeluting with a gradient of 0-5% ethanol in dichloromethane

Sources & evidence

ORD record
ord-50ca4e52ea004a488225d716bea05903
Source dataset
uspto-grants-2005_05
Patent number
US06890923B2

Reaction notes

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