Sodium borohydride → HCID 178432391, compound

HRID 704504Notes

Reaction equation

HRID 704504 reaction equation
[OH:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[N:10]=[C:6]2[N:5]=[C:4]([C:12](OC)=[O:13])[CH:3]=1.[BH4-].[Na+]>C(O)C>[OH:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[N:10]=[C:6]2[N:5]=[C:4]([CH2:12][OH:13])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178498583HCID 178498583, compound

Product 1

HCID 178432391HCID 178432391, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 4 liters of ethanol was suspended 45.4 g of 7-hydroxy-5-methoxycarbonyl-2-methyl-s-triazolo[1,5-a]pyrimidine and 37.83 g of sodium borohydride was added little by little thereto, and the mixture was then stirred at room temperature for 3 hours. A residue obtained by removing ethanol was dissolved in 2 liters of water, and 500 ml of Amberlite IRC-50 (H+) (trade name) was added thereto and stirred. Subsequently, the mixture was filtered and after removing water from the filtrate, 500 ml of methanol was added to the filtrate and the mixture was stirred. Then, methanol was removed from the mixture to obtain a residue. These procedures were repeated three times. Then, 500 ml of ethanol was added to the residue and the mixture was condensed. Precipitated crystals were collected by filtration, washed with ethanol and dried to obtain 39.35 g of the title compound.

Workup

  1. additionwas added little by little thereto, and the mixture
  2. customA residue obtained
  3. customby removing ethanol
  4. dissolutionwas dissolved in 2 liters of water
  5. addition500 ml of Amberlite IRC-50 (H+) (trade name) was added
  6. stirringstirred
  7. filtrationSubsequently, the mixture was filtered
  8. customafter removing water from the filtrate, 500 ml of methanol
  9. additionwas added to the filtrate
  10. stirringthe mixture was stirred
  11. customThen, methanol was removed from the mixture
  12. customto obtain a residue
  13. customcondensed
  14. customPrecipitated crystals
  15. filtrationwere collected by filtration
  16. washwashed with ethanol
  17. customdried

Sources & evidence

ORD record
ord-002a79495d904541806c36115d14ea69
Source dataset
uspto-grants-1991_01
Patent number
US04987129

Reaction notes

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