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

HRID 1010922Notes

Reaction equation

HRID 1010922 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

8

Reactant 5

HCID 222AmmoniaHCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 53244122,6-Dichloropurine

Product 1

HCID 127778192-Chloro-9-(tetrahydropyran-2-yl)adenineYield 93%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2,6-dichloropurine (25 g) in dry ethyl acetate (200 ml) was added p-toluenesulfonic acid monohydrate (235 mg). The reaction was heated to 50° C. and 3,4-dihydro-2H-pyran (18.1 ml) 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

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

Sources & evidence

ORD record
ord-b6bcc4e9826a4848b689b3fa64453318
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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