Methanesulfonic Acid → 6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1778648Notes

Reaction equation

HRID 1778648 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][N:9]=[CH:10][C:5]2=[CH:4][N:3]=1.CS(O)(=O)=O.[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][O:16]3)[N:9]=[CH:10][C:5]2=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 529112546-chloro-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 867228006-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 6-chloro-1H-pyrazolo[3,4-d]pyrimidine (1.00 g, 6.47 mmol) (Ark, Cat. No. AK-30782) in THF (10 mL) at r.t. was added methanesulfonic acid (84 μL, 1.3 mmol), followed by dihydropyran (1.77 mL, 19.4 mmol). The mixture was stirred at r.t. over weekend. The reaction mixture was quenched with saturated aqueous NaHCO3, and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford the crude product which was directly used in the next step reaction without further purification. LCMS (M-84+H)+: m/z=155.1/157.0.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NaHCO3
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-be130cfdf70a4ed7aeb0a4ef8c5631a4
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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