3,4-dihydro-2H-pyran → 6-Bromo-9-(tetrahydro-2H-pyran-2-YL)-9H-purine

HRID 1192522Notes

Reaction equation

HRID 1192522 reaction equation
[Br:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1>C(Cl)(Cl)Cl.O>[Br:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][O:23]1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 178419477HCID 178419477, compound

Product 1

HCID 583686166-Bromo-9-(tetrahydro-2H-pyran-2-YL)-9H-purineYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 6-bromo-9H-purine (2.0 g, 10 mmol) and p-toluenesulfonic acid monohydrate (190 mg, 1.0 mmol) in chloroform (45 mL) at 0° C. was treated with dihydropyran (1.4 mL, 15 mmol) and stirred at 20° C. for 18 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with saturated sodium bicarbonate, water and brine, dried with sodium sulfate, filtered, and concentrated to give a crude residue. Purification by flash column chromatography using ethyl acetate in hexanes (0%-70%) gave the desired product (2.7 g, 94%). LCMS for C10H12BrN4O (M+H)+: m/z=283.0, 285.0; Found: 283.0, 285.0.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organic extracts were washed with saturated sodium bicarbonate, water and brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude residue
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-6f92a7f1cfee4c05be9a747adfe35986
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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