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1,5-Dibromopentane → 2-Amino-5-piperidinomethylpyrrolo[2,3-d]pyrimidin-4-one

HRID 1903312
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1903312
[NH2:1][C:2]1[N:7]=[C:6]2[N:8]=[CH:9][C:10]([CH2:11][NH2:12])=[C:5]2[C:4](=[O:13])[N:3]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.[OH-].[Na+]>CO>[NH2:1][C:2]1[N:7]=[C:6]2[N:8]=[CH:9][C:10]([CH2:11][N:12]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[C:5]2[C:4](=[O:13])[N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 202463772-Amino-5-aminomethylpyrrolo[2,3-d]pyrimidin-4-one

Produkt 1

HCID 204685472-Amino-5-piperidinomethylpyrrolo[2,3-d]pyrimidin-4-oneAusbeute 30,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In 4.5 ml of methanol were dissolved 151 mg of 2-amino-5-aminomethylpyrrolo[2,3-d]pyrimidin-4-one (dihydrochloride) and 138 mg of 1,5-dibromopentane, followed by addition of 2.4 ml of 1 N-sodium hydroxide. The mixture was stirred at room temperature for 4 days. The solvent was then distilled off under pressure and the residue was purified by silica gel column chromatography. The fractions containing the desired compound were pooled and after addition of an excess of hydrogen chloride/ethanol, concentrated to dryness, followed by precipitation with ether to give 45 mg of the desired compound.

Aufarbeitung

  1. distillationThe solvent was then distilled off under pressure
  2. customthe residue was purified by silica gel column chromatography
  3. additionThe fractions containing the desired compound
  4. additionafter addition of an excess of hydrogen chloride/ethanol
  5. concentrationconcentrated to dryness
  6. customfollowed by precipitation with ether

Quellen und Nachweise

ORD-Eintrag
ord-0f71452bb0eb40b192ef1df5e3e0df32
Quelldatensatz
uspto-grants-1984_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04435569

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