Cyclopentylamine → HCID 178503486, compound

HRID 1288425Notes

Reaction equation

HRID 1288425 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[NH:5][C:4]2=[N:10][CH:11]=[CH:12][C:3]=12.[CH:13]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14]1>>[CH:13]1([NH:18][C:2]2[N:7]=[C:6]([S:8][CH3:9])[NH:5][C:4]3=[N:10][CH:11]=[CH:12][C:3]=23)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 178503466HCID 178503466, compound

Product 1

HCID 178503486HCID 178503486, compound

Procedure

To 100 mg of 4-chloro-2-methylthiopyrrolo[2,3-d]pyrimidine was added 2 ml of cyclopentylamine. The solution was heated at reflux under nitrogen for 2 hours. The resulting dark oil was purified by chromatography on 30 g of Sephadex LH-20, elution with H2O and then with increasing concentrations of EtOH up to 40% EtOH. The appropriate fractions were combined and evaporated to dryness and the solid residue was crystallized from EtOH/H2O to afford tan crystals of product, yield 50 mg (40%), m.p. 190°-191° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux under nitrogen for 2 hours
  3. customThe resulting dark oil was purified by chromatography on 30 g of Sephadex LH-20, elution with H2O
  4. temperaturewith increasing concentrations of EtOH up to 40% EtOH
  5. customevaporated to dryness
  6. customthe solid residue was crystallized from EtOH/H2O
  7. customto afford tan crystals of product, yield 50 mg (40%), m.p. 190°-191° C.

Sources & evidence

ORD record
ord-f810da78a9934fca9ff8b15642792817
Source dataset
uspto-grants-1976_10
Patent number
US03988338

Reaction notes

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