Pyridine → HCID 20137146, compound

HRID 2413133Notes

Reaction equation

HRID 2413133 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:12]=[C:11]([NH2:13])[CH:10]=[CH:9][N:8]=1)#[N:2].[CH2:14]([N:17]=[C:18]=S)[CH2:15][CH3:16].[N:20]1C=CC=CC=1>>[CH2:14]([N:17]=[C:18]([NH2:20])[NH:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][C:1]#[N:2])[N:12]=1)[CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 1049PyridineHCID 69403Propyl IsothiocyanateHCID 21279756HCID 21279756, compound

Product 1

HCID 20137146HCID 20137146, compound

Procedure

A mixture of 2-(4-cyanobutyl)-4-aminopyrimidine (1.0 g.), n-propylisothiocyanate (0.57 g.) and pyridine (25 ml.) was heated under reflux for 3 hours. The solvent was removed by evaporation in vacuo and the residue was purified by medium pressure chromatography on silica gel using CHCl3 /MeOH 9.75:0.25 v/v as eluant. The purified product (0.85 g.) in EtOH (10 ml.) was added to EtOH saturated with ammonia (30 ml.) and mercuric oxide (0.6 g.). After 15 minutes the reaction mixture was filtered through diatomaceous earth and the filtrate was evaporated to give 5-(4-[2-propylguanidino]pyrimid-2-yl)valeronitrile (0.85 g.) which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customThe solvent was removed by evaporation in vacuo
  4. customthe residue was purified by medium pressure chromatography on silica gel
  5. additionThe purified product (0.85 g.) in EtOH (10 ml.) was added to EtOH saturated with ammonia (30 ml.) and mercuric oxide (0.6 g.)
  6. filtrationAfter 15 minutes the reaction mixture was filtered through diatomaceous earth
  7. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-65589fb72b964a739a0ddc361a5cc179
Source dataset
uspto-grants-1985_01
Patent number
US04496564

Reaction notes

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