Potassium Carbonate → 1-((R)-tetrahydrofuran-3-yl)-3-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 2365767Notes

Reaction equation

HRID 2365767 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[N:16][C:17]=3[NH2:19])[NH:12][N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].CS(O[C@H:31]1[CH2:35][CH2:34][O:33][CH2:32]1)(=O)=O>CN(C=O)C>[O:33]1[CH2:34][CH2:35][C@@H:31]([N:12]2[C:13]3=[N:14][CH:15]=[N:16][C:17]([NH2:19])=[C:18]3[C:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)=[N:11]2)[CH2:32]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57561588(S)-tetrahydrofuran-3-yl methanesulfonateHCID 178508716HCID 178508716, compound

Product 1

HCID 585067331-((R)-tetrahydrofuran-3-yl)-3-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.5 g, 1.95 mmol), K2CO3 (1.08 g, 7.8 mmol), and (S)-tetrahydrofuran-3-yl methanesulfonate (0.389 g, 2.34 mmol) in DMF (20 mL) was brought to 80° C. under an argon atmosphere. The reaction mixture was left stirring for 3 hours, then cooled and filtered. The filtrate was concentrated in vacuo, but not to dryness. 20 mL of 0.1 sodium citrate was added causing a solid to form, which was collected by filtration to afford 1-((R)-tetrahydrofuran-3-yl)-3-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. ESI-MS m/z [M+H]+ found 327.6, calculated 327.3.

Workup

  1. customwas brought to 80° C. under an argon atmosphere
  2. waitThe reaction mixture was left
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. addition20 mL of 0.1 sodium citrate was added
  7. customto form
  8. filtrationwhich was collected by filtration

Sources & evidence

ORD record
ord-9a35953dd8264654ad6cbb8d98242824
Source dataset
uspto-grants-2014_04
Patent number
US08697709B2

Reaction notes

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