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

HRID 1029556Notes

Reaction equation

HRID 1029556 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 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): δ1.05 (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). Analysis calculated for C8H9N4Cl: C, 48.86; H, 4.61; N, 28.50. Found: C, 49.06; H, 4.76; N, 28.30.

Workup

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

Sources & evidence

ORD record
ord-ab13eacb3bc24ffc825031e98ef6ddd4
Source dataset
uspto-grants-1992_04
Patent number
US05102880

Reaction notes

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