Potassium Carbonate → HCID 44232367, compound

HRID 2189015Notes

Reaction equation

HRID 2189015 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[S:38][C:15]2[N:16]=[CH:17][N:18]([CH2:21][C:22]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=3[F:37])([OH:29])[CH2:23][N:24]3[CH:28]=[N:27][CH:26]=[N:25]3)[C:19](=[O:20])[C:14]=2[CH:13]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[F:37][C:31]1[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:30]=1[C:22]([OH:29])([CH2:23][N:24]1[CH:28]=[N:27][CH:26]=[N:25]1)[CH2:21][N:18]1[C:19](=[O:20])[C:14]2[CH:13]=[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][OH:4])[S:38][C:15]=2[N:16]=[CH:17]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 44232366HCID 44232366, compound

Product 1

HCID 44232367HCID 44232367, compoundYield 90.57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6-(7-Acetoxyheptyl)-3-[2-(2,4-difluorophenyl)-2-hydroxy-3-[1,2,4]triazol-1-ylpropyl]-thieno[2,3-d]pyrimidin-4(3H)-one (3.00 g, 5.5 mmol) was dissolved in the mixture of methanol (10 ml) and water (2 ml). Then potassium carbonate (760 mg, 5.5 mmol) was added and the mixture was stirred at RT for 2 hours. Methanol was then removed on rotavapor, water (10 ml) was added to the reaction mixture and extracted with ethyl acetate (2×5 ml), dried, concentrated and purified by column chromatography to obtain the pure 3-[2-(2,4-difluorophenyl)-2-hydroxy-3-[1,2,4]triazol-1-yl-propyl]-6-(7-hydroxyheptyl)-thieno[2,3-d]pyrimidin-4(3H)-one (2.5 gm, 90.57%).

Workup

  1. customMethanol was then removed on rotavapor, water (10 ml)
  2. additionwas added to the reaction mixture
  3. extractionextracted with ethyl acetate (2×5 ml)
  4. customdried
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-4eb55276234c404d96df99fd85526e00
Source dataset
uspto-grants-2012_12
Patent number
US08324227B2

Reaction notes

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