Sodium cyanoborohydride → HCID 135621395, compound

HRID 2050505Notes

Reaction equation

HRID 2050505 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([CH3:21])[C:17]([C:18]([NH2:20])=[O:19])=[C:13]2[N:12]=[CH:11][CH:10]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([CH3:21])[C:17]([C:18]([NH2:20])=[O:19])=[C:13]2[NH:12][CH2:11][CH:10]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 14501858HCID 14501858, compound

Product 1

HCID 135621395HCID 135621395, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 3.21 g portion of 7-(2,5-dichlorophenyl)-2methylpyrazolo(1,5-a)pyrimidine-3-carboxamide (Example 2) is suspended in 150 ml of glacial acetic acid and stirred under nitrogen at room temperature. Then 1.5 g of sodium cyanoborohydride is added in portions and stirring is continued for 3 hours. The reaction mixture is evaporated to dryness in vacuo and when water is added to the residue a white precipitate forms. This solid is collected and dissolved in dichloromethane, and this solution is washed with an aqueous saturated solution of sodium bicarbonate. Then the organic phase is dried over anhydrous sodium sulfate and filtered. The filtrate is evaporated in vacuo and gives 2.95 g of the product of this example as a white solid, mp 93-96° C.

Workup

  1. stirringstirring
  2. customThe reaction mixture is evaporated to dryness in vacuo and when water
  3. additionis added to the residue a white precipitate forms
  4. customThis solid is collected
  5. dissolutiondissolved in dichloromethane
  6. washthis solution is washed with an aqueous saturated solution of sodium bicarbonate
  7. dry with materialThen the organic phase is dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-51fbca5b502646a5aa04d4cde6c534bc
Source dataset
uspto-grants-1991_05
Patent number
US05013737

Reaction notes

Loading…