3,4-dihydro-2H-pyran → 2,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

HRID 527760Notes

Reaction equation

HRID 527760 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.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>C1(C)C=CC(S(O)(=O)=O)=CC=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:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 53244122,6-Dichloropurine

Product 1

HCID 2702652,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineYield 102.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To 2,6-dichloropurine (25.0 g) (available from, for example, Aldrich, UK) 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 (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-b0a46d3f0d2d4e89a67bc3ef177e21ac
Source dataset
uspto-grants-2016_05
Patent number
US09346806B2

Reaction notes

Loading…