p-Toluenesulfonic acid → 6-Chloro-8-propyl-9H-purine

HRID 1729403Notes

Reaction equation

HRID 1729403 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.CO[C:12](OC)(OC)[CH2:13][CH2:14][CH3:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>COCCO>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]2[C:7]=1[NH:8][C:12]([CH2:13][CH2:14][CH3:15])=[N:1]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 780104,5-Pyrimidinediamine, 6-chloro-HCID 1235121,1,1-Trimethoxybutane

Product 1

HCID 190122236-Chloro-8-propyl-9H-purine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

To a solution of 4,5-diamino-6-chloropyrimidine (0.289 g, 2 mmol) in 2-methoxyethanol (10 ml) were added trimethylorthobutyrate (0.5 ml, 3 mmol) and p-toluenesulfonic acid (0.03 g), and the mixture was refluxed for 18 hours and then concentrated in vacuo. The residue was partitioned between water and and ethylacetate. The organic phase was then washed with brine and dried (MgSO4). The crude product obtained after evaporation of the solvent was purified by flash column chromatography on silica-gel using ethylacetate/hexane (1:1). The fractions containing pure product were pooled and concentrated in vacuo, and then allowed to stand at room temperature overnight. The crystalline product was filtered and dried. Yield 0.17 g (43%); NMR (CDCl3): δ 1.05 (t, J=9 Hz, 3H), 2.0 (q, 2H), 3.1 (q, 2H), 8.74 (s, 1H); FAB mass-spectra: m/e 197 and 199 (M+H).

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between water and and ethylacetate
  4. washThe organic phase was then washed with brine
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-7ee3114b5fde466e881277b57a16c6ed
Source dataset
uspto-grants-1994_07
Patent number
US05332744

Reaction notes

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