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93366-88-2

93366-88-2 Structure

93366-88-2 Structure
IdentificationBack Directory
[Name]

1H-Pyrrolo[2,3-d]pyrimidin-2-amine (9CI)
[CAS]

93366-88-2
[Synonyms]

2-AMino-7H-pyrrolo[2,3-d]...
7H-Pyrrolo[2,3-d]pyrimidin-2-amin
2-Amino-7H-pyrrolo<2,3-d>pyrimidin
1H-Pyrrolo[2,3-d]pyrimidin-2-amine
7H-Pyrrolo[2,3-d]pyriMidin- 2-aMine
2-Amino-7H-pyrrolo[2,3-d]pyrimidine
1H-Pyrrolo[2,3-d]pyrimidin-2-amine (9CI)
[Molecular Formula]

C6H6N4
[MDL Number]

MFCD12923656
[MOL File]

93366-88-2.mol
[Molecular Weight]

134.14
Chemical PropertiesBack Directory
[Boiling point ]

359.8±25.0 °C(Predicted)
[density ]

1.61±0.1 g/cm3(Predicted)
[storage temp. ]

Keep in dark place,Inert atmosphere,Room temperature
[pka]

12.05±0.20(Predicted)
[Appearance]

White to off-white Solid
Spectrum DetailBack Directory
[Spectrum Detail]

1H-Pyrrolo[2,3-d]pyrimidin-2-amine (9CI)(93366-88-2)1HNMR
Hazard InformationBack Directory
[Synthesis]

2-Amino-4-chloropyrrolo[2,3-d]pyrimidine

84955-31-7

1H-Pyrrolo[2,3-d]pyrimidin-2-amine (9CI)

93366-88-2

General procedure for the synthesis of 2-amino-7H-pyrrolo[2,3-D]pyrimidines from 2-amino-4-chloropyrrolo[2,3-D]pyrimidines: 2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidines (1) (1.0 g, 6.0 mmol) were suspended in methanol (50 mL) and an aqueous ammonium hydroxide solution (1 mL), and 10% Pd-C catalyst ( 500 mg). The reaction mixture was stirred at atmospheric pressure for 17 h. Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad. The filtrate was concentrated and purified by silica gel column chromatography (eluent ratio of dichloromethane: methanol = 90:10) to afford 717 mg of the target product 2-amino-7H-pyrrolopyrimidine in 90% yield. The structure of the product was confirmed by 1H NMR (DMSO-D6): δ 11.4 (broad single peak, 1H), 8.50 (single peak, 1H), 7.11 (double peak, J=3.6,0.6Hz, 1H), 6.49 (broad single peak, 2H), 6.32 (double peak, J=3.6,0.9Hz, 1H).

[References]

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 18, p. 5261 - 5264
[2] Patent: WO2004/80466, 2004, A1. Location in patent: Page/Page column 32
[3] Liebigs Annalen der Chemie, 1984, # 10, p. 1719 - 1730
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 334 - 337
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