Sodium cyanoborohydride → HCID 14677484, compound

HRID 477458Notes

Reaction equation

HRID 477458 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[N:14]3[CH:15]=[N:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:4]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[F:21][C:2]([F:1])([F:22])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[CH:15]=[N:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 146774714-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxamide

Product 1

HCID 14677484HCID 14677484, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 9.2 g of 4-(α,α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxamide (Ex. 28, U.S. Pat. No. 4,236,005) in 100 ml of glacial acetic acid, was added in portions 3.0 g of sodium cyanoborohydride at room temperature under nitrogen. The mixture was stirred at room temperature for 3 hours. The solvent was evaporated in vacuo to give an oil. The oil was triturated with water and a white precipitate formed, and this was collected by filtration, washed with water and then was slurried with saturated sodium bicarbonate solution. The precipitate was again collected by filtration and washed with water. This solid was dissolved in dichloromethane, and then water was added. The organic layer was separated, dried over anhydrous sodium sulfate and filtered. Evaporation of the filtrate gave a yellow solid which was recrystallized from acetonitrile to give 7.0 g of the product of the example as a light yellow solid, mp 192°-194° C.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give an oil
  3. customThe oil was triturated with water
  4. customa white precipitate formed
  5. filtrationthis was collected by filtration
  6. washwashed with water
  7. filtrationThe precipitate was again collected by filtration
  8. washwashed with water
  9. dissolutionThis solid was dissolved in dichloromethane
  10. additionwater was added
  11. customThe organic layer was separated
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. customEvaporation of the filtrate
  15. customgave a yellow solid which
  16. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-7de5d1718ed94ea8a38e196896320ea1
Source dataset
uspto-grants-1989_12
Patent number
US04888345

Reaction notes

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