Potassium Carbonate → 1-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 238011

Reaktionsgleichung

Reaktionsgleichung von HRID 238011
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C=O)C>[CH:19]1([N:4]2[C:5]3=[N:6][CH:7]=[N:8][C:9]([NH2:11])=[C:10]3[C:2]([I:1])=[N:3]2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 73784IodocyclopentaneHCID 178508725HCID 178508725, Verbindung

Produkt 1

HCID 223468081-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (400 mg, 1.53 mmol) and K2CO3 (1 g, 6 mmol) in DMF (5 ml) was stirred at room temperature under an argon atomosphere. Iodocyclopentane (1.0 g, 0.0084 mol) was added with a syringe. Reaction was refluxed under argon atmosphere for 2 hours. Solid K2CO3 was removed by filtration. Solvent was partially removed in vacuo. Sodium citrate (50 ml) was added and reaction was extracted with EtOAc. Organic phases concentrated in vacuo and purified using silica gel column chromatography [MeOH—CH2Cl2, 5:95] yielding BA80 (300 mg, 60% yield). ESI-MS (M+H)+ m/z calcd 330.0, found 330.0.

Aufarbeitung

  1. customReaction
  2. temperaturewas refluxed under argon atmosphere for 2 hours
  3. customSolid K2CO3 was removed by filtration
  4. customSolvent was partially removed in vacuo
  5. additionSodium citrate (50 ml) was added
  6. customreaction
  7. extractionwas extracted with EtOAc
  8. concentrationOrganic phases concentrated in vacuo
  9. custompurified
  10. customyielding BA80 (300 mg, 60% yield)

Quellen und Nachweise

ORD-Eintrag
ord-99fa0499fb4c4f1494e05ecd28b77800
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642604B2

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