Sodium Acetate → HCID 20092866, compound

HRID 274255Notes

Reaction equation

HRID 274255 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH2:11][CH2:12][CH3:13])[C:3]=1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]#[N:28])=[CH:17][CH:16]=1.C([O-])(=O)C.[Na+]>COCCO>[C:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][C:3]2[C:4]([CH2:11][CH2:12][CH3:13])=[N:5][C:6]3[N:7]([N:8]=[CH:9][CH:10]=3)[CH:2]=2)=[CH:16][CH:17]=1)#[N:28]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 20092843HCID 20092843, compound

Product 1

HCID 20092866HCID 20092866, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of 5.4 g of the chlorinated compound prepared in Example 27 in 110 ml of 2-methoxyethanol containing 1.2 g of anhydrous sodium acetate is hydrogenated, at atmospheric pressure and ambient temperature, in the presence of 1.4 g of 5% Pd-on-charcoal. The system is purged with nitrogen. The catalyst is filtered off on Celite 545 and washed with 2-methoxyethanol. The filtrate is concentrated and taken up in ether to give 5.2 g of crude product. Purification by chromatography on silica gel (eluent: dichloromethane 90%/acetone 10%) gives 4 g of 6-[(2'-cyanobiphenyl-4yl)methyl]-5-propylpyrazolo[1,5-a]pyrimidine.

Workup

  1. customThe system is purged with nitrogen
  2. filtrationThe catalyst is filtered off on Celite 545
  3. washwashed with 2-methoxyethanol
  4. concentrationThe filtrate is concentrated
  5. customto give 5.2 g of crude product
  6. customPurification by chromatography on silica gel (eluent: dichloromethane 90%/acetone 10%)

Sources & evidence

ORD record
ord-51cc1229e1d545cfa7209cb3f0a5e857
Source dataset
uspto-grants-1995_02
Patent number
US05389632

Reaction notes

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