Sodium cyanoborohydride → HCID 135671363, compound

HRID 231528Notes

Reaction equation

HRID 231528 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][CH:17]=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[F:18][C:2]([F:1])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][CH:17]=[C:13]3[NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 197562037-[3-(Trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine

Product 1

HCID 135671363HCID 135671363, compoundYield 24.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 25.0 g of 7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine in 250 ml of glacial acetic acid, at room temperature, under nitrogen was added portionwise 14.92 g of sodium cyanoborohydride. The resultant solution was stirred for 24 hours, and then was evaporated in vacuo to give an oil. The oil was dissolved in chloroform and washed with saturated sodium bicarbonate. The organic layer was separated, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo to give a semi-solid which was chromatographed on a silica gel column using a mixture of 25% ethyl acetate and 75% hexane as the solvent system. The product fraction was collected and evaporated to give 6.2 g of the desired product as orange crystals, mp 61°-64° C.

Workup

  1. customwas evaporated in vacuo
  2. customto give an oil
  3. washwashed with saturated sodium bicarbonate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo
  8. customto give a semi-solid which
  9. customwas chromatographed on a silica gel column
  10. additiona mixture of 25% ethyl acetate and 75% hexane as the solvent system
  11. customThe product fraction was collected
  12. customevaporated

Sources & evidence

ORD record
ord-ffcc17ed6f1145efb091c0b8192fa51c
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Reaction notes

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