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

HRID 1168278Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([Cl:11])[N:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:24]1[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25]1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][O:24]2)=[C:4]([Cl:11])[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2,6-Dichloro-9H-purine (20 g, 0.11 mol) and 4-toluenesulphonic acid monohydrate (0.2 g) were dissolved in ethyl acetate (300 ml), the mixture was heated to 50° C. and a solution of 2,3-dihydropyran (12.6 ml, 0.14 mol) in ethyl acetate (50 ml) was added slowly over 30 minutes. The reaction mixture was then cooled to room temperature, water (100 ml) was added and the pH of the solution was adjusted to 7 with a saturated aqueous solution of sodium hydrogen carbonate. The layers were separated and the organic layer was washed sequentially with water and brine, dried (anhydrous magnesium sulphate), filtered and evaporated under reduced pressure. The residue was twice azeotroped from pentane to afford the title compound as a slightly impure white solid (30.9 g).

Workup

temperatureThe reaction mixture was then cooled to room temperature
customThe layers were separated
washthe organic layer was washed sequentially with water and brine
dry with materialdried (anhydrous magnesium sulphate)
filtrationfiltered
customevaporated under reduced pressure
customThe residue was twice azeotroped from pentane

Sources & evidence

ORD record: ord-4be9a9a3109c4ecaac10e2d759e046cd
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06624158B2

Reaction notes

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