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Hydrochloric Acid → 2-[4-Amino-5-(4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]-2-methylpropionamide

HRID 51501
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 51501
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[Na+].Br[C:27]([CH3:32])([CH3:31])[C:28]([NH2:30])=[O:29].Cl>CN1CCCN(C)C1=O.O>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)=[CH:9][N:8]([C:27]([CH3:32])([CH3:31])[C:28]([NH2:30])=[O:29])[C:4]=2[N:5]=[CH:6][N:7]=1
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Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1012352-Bromo-2-methylpropanamide2×HCID 120422345-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Produkt 1

HCID 227362342-[4-Amino-5-(4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]-2-methylpropionamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×
HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Lösungsmittel

Versuchsvorschrift

4-Amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine (200 mg) was dissolved in 1,3-dimethyl-3,4,5,6-tetrahydro-2-(1H)-pyrimidinone (1.5 ml) with stirring and sodium hydroxide (0.158 g) was added at ambient temperature and the mixture stirred for 15 minutes. 2-Bromo-2-methylpropanamide (0.5 g) was added and the mixture was stirred vigorously for 18 hours at ambient temperature under a water-free atmosphere, then further 2-bromo-2-methylpropanamide (0.15 g) was added and stirred for a further 24 hours. Water (3 ml) was added to the reaction mixture together with dilute hydrochloric acid (5M) to adjust the pH to 0. The suspension was added to water (60 ml) and the mixture left to stand for 18 hours at ambient temperature. The solid was collected by filtration, washed well with water and dried under high vacuum at 50° C. The solid was purified by preparative HPLC (reverse phase). Appropriate fractions were collected and combined and extracted with dichloromethane. Evaporation of the dichloromethane gave 2-[4-amino-5-(4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]-2-methylpropionamide, m.p. 227-228° C.

Aufarbeitung

  1. stirringthe mixture stirred for 15 minutes
  2. stirringthe mixture was stirred vigorously for 18 hours at ambient temperature under a water-free atmosphere
  3. stirringstirred for a further 24 hours
  4. waitthe mixture left
  5. filtrationThe solid was collected by filtration
  6. washwashed well with water
  7. customdried under high vacuum at 50° C
  8. customThe solid was purified by preparative HPLC (reverse phase)
  9. customAppropriate fractions were collected
  10. extractionextracted with dichloromethane
  11. customEvaporation of the dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-fd31b76a3bbf4949ac2f97e1e31b5090
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06713474B2

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