HCID 178509655, compound → HCID 178509654, compound

HRID 274110Notes

Reaction equation

HRID 274110 reaction equation
C([O:8][CH2:9][C:10]1[N:15]2[N:16]=[CH:17][N:18]=[C:14]2[N:13]=[C:12]([OH:19])[C:11]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]#[N:34])=[CH:23][CH:22]=1)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[C:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[CH:23]=[CH:22][C:21]([CH2:20][C:11]2[C:12]([OH:19])=[N:13][C:14]3[N:15]([N:16]=[CH:17][N:18]=3)[C:10]=2[CH2:9][OH:8])=[CH:26][CH:25]=1)#[N:34]

Participants

4

Reactant 1

HCID 178509655HCID 178509655, compound

Product 1

HCID 178509654HCID 178509654, compoundYield 30.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 9 g of the compounds prepared in Example 43 in 360 ml of acetic acid is reduced by catalytic hydrogenation in the presence of 1.8 g of 5% palladium-on-charcoal. The reaction is carried out at atmospheric pressure and at 50° C. The catalyst is filtered off on Celite 545 and washed with acetic acid and the filtrate is concentrated and then purified by chromatography on silica gel (eluent: chloroform 95%/methanol 5%) to give 4.5 g of the starting material and 2.2 g of 6-[(2'-cyanobiphenyl-4-yl)methyl]-5-hydroxy-7-hydroxymethyl-1,2,4-triazolo[1,5-a]pyrimidine.

Workup

  1. customis carried out at atmospheric pressure and at 50° C
  2. filtrationThe catalyst is filtered off on Celite 545
  3. washwashed with acetic acid
  4. concentrationthe filtrate is concentrated
  5. custompurified by chromatography on silica gel (eluent: chloroform 95%/methanol 5%)

Sources & evidence

ORD record
ord-cad6dfb2e58b4886b7225ec86f1acf23
Source dataset
uspto-grants-1995_02
Patent number
US05387747

Reaction notes

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