HCID 178444753, compound → HCID 178444748, compound

HRID 1288426Notes

Reaction equation

HRID 1288426 reaction equation
[CH2:1]([NH:7][C:8]1[N:13]=[C:12](SC)[NH:11][C:10]2=[N:16][CH:17]=[CH:18][C:9]=12)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>[Ni]>[CH2:1]([NH:7][C:8]1[N:13]=[CH:12][NH:11][C:10]2=[N:16][CH:17]=[CH:18][C:9]=12)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 1

HCID 178444753HCID 178444753, compound

Product 1

HCID 178444748HCID 178444748, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst2×

Procedure

Into a flask equipped with a stirring bar and reflux condenser were introduced 4-(n-hexylamino)-2-methylthio-pyrrolo[2,3-d]-pyrimidine (100 mg) and 5 ml of Raney nickel ethanolic slurry (c.a. 0.6 g/ml; 10 months old). The mixture was heated at reflux and additional 5 ml portions of Raney nickel slurry were added at 12 hour intervals for 48 hours at which point tlc (24:1 CHCl3 -MeO) indicated that the reaction was complete. The Raney nickel was removed by filtration through Celite. Evaporation of the solvent afforded a tan solid (79 mg; 95%) which was purified by preparative tlc on silica using a solvent system of 4:1 benzene-ethanol. This purification yielded a white solid, m.p. 147°-148° C.; C12H18N4 (M+ calculated: 218.15314; found: 218.15365);

Workup

  1. customInto a flask equipped with a stirring bar
  2. temperaturereflux condenser
  3. temperatureThe mixture was heated
  4. temperatureat reflux
  5. customThe Raney nickel was removed by filtration through Celite
  6. customEvaporation of the solvent
  7. customafforded a tan solid (79 mg; 95%) which
  8. customwas purified by preparative tlc on silica using a solvent system of 4:1 benzene-ethanol
  9. customThis purification
  10. customyielded a white solid, m.p. 147°-148° C.

Sources & evidence

ORD record
ord-05ac28a294bb448f9fe736f10c7ba1f4
Source dataset
uspto-grants-1976_10
Patent number
US03988338

Reaction notes

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