p-Toluenesulfonic acid → 2,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

HRID 2038156Notes

Reaction equation

HRID 2038156 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1>C(OCC)(=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][O:23]2)=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 53244122,6-Dichloropurine

Product 1

HCID 2702652,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To 2,6-dichloropurine (commercially available, for example, from Aldrich) (25.0 g) was added ethyl acetate (260 mL), followed by p-toluenesulfonic acid (0.253 g). The mixture was heated to 50° C. and then 3,4-dihydro-2H-pyran (commercially available, for example, from Aldrich) (16.8 g) was added. The reaction mixture was then heated at 50° C. for 4 hours. The reaction mixture was evaporated in vacuo to give the title compound as a yellow solid (36.9 g).

Workup

  1. temperatureThe reaction mixture was then heated at 50° C. for 4 hours
  2. customThe reaction mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-0029a5b6100943789789fd4a11206fd2
Source dataset
uspto-grants-2013_11
Patent number
US08575340B2

Reaction notes

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