Ammonia → 2-Chloro-9-(tetrahydropyran-2-yl)adenine

HRID 2367958Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[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.O.[NH3:31]>C(OCC)(=O)C.C(O)(C)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:29]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:4]([NH2:31])[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2,6-dichloropurine (25 g) (commercially available from, for example, Aldrich) in dry ethyl acetate (200 mL) was added p-toluenesulfonic acid monohydrate (235 mg) (commercially available from, for example, Aldrich). The reaction was heated to 50° C. and 3,4-dihydro-2H-pyran (18.1 ml) (commercially available from, for example, Aldrich) was added in one go. The reaction was allowed to stir at 50° C. for 1 hour and the solvent was removed under reduced pressure. This afforded a yellow solid. A suspension of this solid (˜36 g) in 2.0M ammonia in isopropanol (460 mL) was heated under nitrogen at 60° C. for 4 hours with an attached condenser. The reaction was poured into water (50 mL) and left to cool overnight. The precipitate was filtered and dried on a rotary evaporator (60° C.) for 30 minutes to afford the title compound as an off-white solid, 31 g (93%, 2 steps).

Workup

customthe solvent was removed under reduced pressure
customThis afforded a yellow solid
temperaturewas heated under nitrogen at 60° C. for 4 hours with an attached condenser
waitleft
temperatureto cool overnight
filtrationThe precipitate was filtered
customdried on a rotary evaporator (60° C.) for 30 minutes

Sources & evidence

ORD record: ord-13705d49e9cb40c4b3b25ea00ab65337
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703754B2

Reaction notes

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