Methanol → HCID 66915353, compound

HRID 1931778Notes

Reaction equation

HRID 1931778 reaction equation
[CH3:1][O-:2].[Na+].[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:21]3=[N:22][C:23](Cl)=[N:24][C:25](Cl)=[C:20]3[CH:19]=[N:18]2)[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].[CH3:28][OH:29]>>[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:21]3=[N:22][C:23]([O:29][CH3:28])=[N:24][C:25]([O:2][CH3:1])=[C:20]3[CH:19]=[N:18]2)[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 57964878HCID 57964878, compound2×

Product 1

HCID 66915353HCID 66915353, compound

Procedure

Sodium methoxide (4 mmol) is added to a mixture of 4-(4,6-dichloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 24; 1 mmol) in methanol. The resulting mixture is heated at reflux for 8 h and then cooled. The solvent is evaporated, and ethyl acetate and water are added. The organic layer is washed with water and brine, dried (magnesium sulfate), filtered, evaporated, and purified by flash chromatography on silica gel to give 4-(4,6-dimethoxy-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 8 h
  3. temperaturecooled
  4. customThe solvent is evaporated
  5. additionethyl acetate and water are added
  6. washThe organic layer is washed with water and brine
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. customevaporated
  10. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-41e502a1375f4766a69cc75af44e2f5c
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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