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

HRID 1042261Notes

Reaction equation

HRID 1042261 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>CCOC(C)=O.CC1C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 178478393HCID 178478393, compound

Product 1

HCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineYield 99.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 6-chloro-9H-purine (25.36 g, 164 mmol) and 4-methylbenzenesulfonic acid (0.565 g, 3.28 mmol) in EtOAc (250 mL) was treated with 3,4-dihydro-2H-pyran (44.9 mL, 492 mmol). The mixture was heated at 90° C. and the solid slowly dissolved over 1 h. The flask was removed from the oil bath and the cloudy, yellow solution was filtered and concentrated in vacuo. The pale yellow residue was dissolved in DCM and purified by flash chromatography (50% EtOAc/hexane) (1 L silica/4 L solvent) to give 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (38.90 g, 99.3% yield) as a colorless oil which slowly crystallized. MS (ESI, pos. ion) m/z: 239.1 [M+H]+

Workup

  1. dissolutionthe solid slowly dissolved over 1 h
  2. customThe flask was removed from the oil bath
  3. filtrationthe cloudy, yellow solution was filtered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe pale yellow residue was dissolved in DCM
  6. custompurified by flash chromatography (50% EtOAc/hexane) (1 L silica/4 L solvent)

Sources & evidence

ORD record
ord-d7b9104d4d1e4aa28fa3c8b21077e8f5
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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