| Identification | Back Directory | [Name]
3H-Pyrrolo[2,3-d]pyrimidine-5-carbonitrile, 2-amino-4,7-dihydro-4-oxo- | [CAS]
69205-79-4 | [Synonyms]
PreQ0
7-Cyano-7-deazaguanine
2-Amino-4-oxo-3H,4H,7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
2-AMino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyriMidine-5-carbonit
2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidine-5-carbonitrile
2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
2-amino-4,7-dihydro-4-oxo-3H-Pyrrolo[2,3-d]pyrimidine-5-carbonitrile
2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
3H-Pyrrolo[2,3-d]pyrimidine-5-carbonitrile, 2-amino-4,7-dihydro-4-oxo- | [Molecular Formula]
C7H5N5O | [MDL Number]
MFCD13178502 | [MOL File]
69205-79-4.mol | [Molecular Weight]
175.15 |
| Chemical Properties | Back Directory | [Melting point ]
>250 °C | [Boiling point ]
585.1±60.0 °C(Predicted) | [density ]
1.87±0.1 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [pka]
13.95±0.20(Predicted) | [Appearance]
Light brown to brown Solid | [InChI]
InChI=1S/C7H5N5O/c8-1-3-2-10-5-4(3)6(13)12-7(9)11-5/h2H,(H4,9,10,11,12,13) | [InChIKey]
FMKSMYDYKXQYRV-UHFFFAOYSA-N | [SMILES]
C1(N)NC(=O)C2C(C#N)=CNC=2N=1 |
| Hazard Information | Back Directory | [Uses]
2-Amino-4-oxo-3H,4H,7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile is a reagent used for structure-based design and synthesis of antiparasitic pyrrolopyrimidines targeting pteridine reductase 1. | [Definition]
ChEBI: 7-cyano-7-deazaguanine is a pyrrolopyrimidine that is 7-deazaguanine substituted at position 7 by a cyano group. It has a role as an Escherichia coli metabolite. It is a pyrrolopyrimidine and a nitrile. It is functionally related to a 7-carboxy-7-deazaguanine. | [Synthesis]
GENERAL PROCEDURE: Preparation of 4-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile: To a solution of trace water (90 mL) containing sodium acetate (6.4 g, 76 mmol) was added 2,4-diamino-6-hydroxypyrimidine (3.00 g, 24 mmol), and stirred for 1 hour at 50 °C. Maintaining the temperature at 50 °C, a solution of crude 2-chloro-2-formylacetonitrile (3.00 g, 32 mmol) in deionized water (44 mL) was slowly added dropwise through a dropping funnel, and the reaction mixture gradually changed to a beige color. The reaction temperature was then raised to 80 °C and heating was continued for 18 hours. After that, the reaction temperature was further raised to 100 °C and maintained for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and the solid was collected by filtration. The resulting solid was suspended in ethanol and saturated aqueous KOH solution was added dropwise until the solid was completely dissolved. Activated carbon was added to the solution and the solid was removed by filtration after stirring for 30 minutes. The pH of the filtrate was adjusted to 6 with concentrated aqueous hydrochloric acid, at which time a precipitate was generated and collected by filtration. For complete removal of residual water, the solid was dissolved in a solvent mixture of toluene/methanol (1:1) and subsequently concentrated under reduced pressure. Finally, the obtained solid was dried over P2O5 to afford the target compound 4-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (1.68 g, 9.6 mmol, 40% yield) as a beige solid. The synthesis is referenced from Brooks 2012.1H NMR (400 MHz, DMSO-d6) δ 11.98 (br s, 1H), 10.74 (br s, 1H), 7.59 (s, 1H), 6.43 (s, 2H). 13C NMR (100 MHz, DMSO-d6) δ 158.0, 154.3, 152.1, 128.2, 116.4, 99.2, 86.0. HRMS (m/z ESI): [C7H5N5O - H]? Calculated value 174.0416, measured value 174.0415. | [References]
[1] Tetrahedron Letters, 2006, vol. 47, # 32, p. 5747 - 5750
[2] Advanced Synthesis and Catalysis, 2012, vol. 354, # 11-12, p. 2191 - 2198
[3] Patent: WO2016/50806, 2016, A1. Location in patent: Page/Page column 22; 23
[4] Patent: WO2016/50804, 2016, A1. Location in patent: Page/Page column 20 |
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