Sodium cyanoborohydride → 4-(3-Chlorophenyl)-1,2-dihydroimidazo[1,5-a]pyrimidine-8-carboxamide

HRID 1199954Notes

Reaction equation

HRID 1199954 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[CH:14]=[N:15][C:16]([C:17]([NH2:19])=[O:18])=[C:12]3[N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[CH:14]=[N:15][C:16]([C:17]([NH2:19])=[O:18])=[C:12]3[NH:11][CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 146774724-(3-Chlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamide

Product 1

HCID 146774854-(3-Chlorophenyl)-1,2-dihydroimidazo[1,5-a]pyrimidine-8-carboxamideYield 59.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.39 g of 4-(m-chlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamide (Example 14) in 100 ml of glacial acetic acid, was added in portions 2.8 g of sodium cyanoborohydride at room temperature under nitrogen. The mixture was stirred at room temperature for 2 hours. The solvent was evaporated in vacuo to give an oil, and this was dissolved in dichloromethane, then washed with saturated sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate and filtered through a short column of hydrous magnesium silicate. Evaporation of the solvent gave a yellow solid which was recrystallized from acetonitrile to give 3.25 g of the desired product as a yellow solid, mp 182°-184° C.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give an oil
  3. washwashed with saturated sodium bicarbonate solution
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered through a short column of hydrous magnesium silicate
  7. customEvaporation of the solvent
  8. customgave a yellow solid which
  9. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-bab6e77ff26c432b9557443259528f46
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

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