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

HRID 897099Notes

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 3,4-dihydro-2H-pyran (12.6 ml, 0.14 mol) in ethyl acetate (50 ml) was added slowly over 30 minutes. The reaction mixture was cooled to room temperature, water (100 ml) was added and the pH of the solution was adjusted to 7 by addition of a saturated aqueous solution of sodium hydrogen carbonate. The organic layer was separated, washed sequentially with water and brine, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The residue was azeotroped with pentane (100 ml) to afford the title compound as a slightly impure white solid (30.9 g).

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe organic layer was separated
washwashed sequentially with water and brine
dry with materialdried over anhydrous magnesium sulphate
filtrationfiltered
customevaporated under reduced pressure
customThe residue was azeotroped with pentane (100 ml)

Sources & evidence

ORD record: ord-0dd0e902ed2045eeb36ac7d7e56a24de
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921753B2

Reaction notes

Loading…