Methanol → HCID 59311386, compound

HRID 1693322Notes

Reaction equation

HRID 1693322 reaction equation
I([O-])(=O)(=O)=O.[Na+].[Cl:7][C:8]1[N:13]=[C:12]([N:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[N:11]=[C:10]2[N:29]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=3)[N:30]=[C:31]([CH2:32][CH:33]([OH:36])CO)[C:9]=12.O1CCCC1.CO>O>[Cl:7][C:8]1[N:13]=[C:12]([N:14]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[N:11]=[C:10]2[N:29]([CH2:37][C:38]3[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=3)[N:30]=[C:31]([CH2:32][CH2:33][OH:36])[C:9]=12

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 23667635Sodium periodateHCID 58201194HCID 58201194, compound

Product 1

HCID 59311386HCID 59311386, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium periodate (19 g) was added to a mixture composed of the above di-tert-butyl {4-chloro-3-(2,3-dihydroxypropyl)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl}imidodicarbonate (10 g), tetrahydrofuran (100 ml), methanol (100 ml) and water (100 ml) under cooling in an ice bath, and the mixture was stirred at room temperature for one hour. The reaction mixture was separated with water (600 mL) and ethyl acetate (400 mL). The organic layer was washed with brine, and then dried over anhydrous sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. Methanol (200 mL) was added to the resulting residue. Sodium borohydride (1000 mg) was added under cooling in an ice bath, and the mixture was stirred for one hour. Water (400 ml) was added to the reaction mixture, followed by extraction with ethyl acetate (300 ml) twice. Then, the organic layers were washed with brine. The organic layers were dried over anhydrous sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure and the solvent was evaporated to obtain the title compound (8.5 g, 90%) as an oil.

Workup

  1. temperatureunder cooling in an ice bath
  2. customThe reaction mixture was separated with water (600 mL) and ethyl acetate (400 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThen, the filtrate was concentrated under reduced pressure
  7. additionMethanol (200 mL) was added to the resulting residue
  8. additionSodium borohydride (1000 mg) was added
  9. temperatureunder cooling in an ice bath
  10. stirringthe mixture was stirred for one hour
  11. additionWater (400 ml) was added to the reaction mixture
  12. extractionfollowed by extraction with ethyl acetate (300 ml) twice
  13. washThen, the organic layers were washed with brine
  14. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  15. filtrationfiltered
  16. concentrationThen, the filtrate was concentrated under reduced pressure
  17. customthe solvent was evaporated

Sources & evidence

ORD record
ord-581dea064d044ff9828e46d8b1a07744
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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