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1-(6-Amino-9H-purin-9-yl)-3-diazoacetone

Department of Medicinal Chemistry, A. Szent-Györgyi Medical University, Dóm tér 8., H-6720 Szeged, Hungary
Molecules 2000, 5(1), M130; https://doi.org/10.3390/M130
Submission received: 21 December 1999 / Accepted: 14 January 2000 / Published: 24 January 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 05 m130 i001
Adenine (1, 0.676 g, 5.0 mmol) was suspended in anhydrous DMF (20 mL) and sodium hydride (55-60 % suspension in mineral oil, 0.262 g, 6.0 mmol) was added at room temperature. The mixture was vigorously stirred at 100 °C for 1 h and then cooled to room temperature. 1-Bromo-3-diazo-propan-2-one (2 [1,2], 0.978 g, 6.0 mmol) was added dropwise at this temperature. The reaction mixture immediately turned brown and the initial sodium adenide dissolved. The mixture was set aside at room temperature. After 16 h t.l.c. (20 % v/v methanol in dichloromethane) indicated that the reaction mixture still contained significant amounts of unreacted adenine. After evaporating the solvent in vacuo the residue was successively coevaporated with toluene (2 x) and ethanol (2 x). Chromatographic purification (5-8 % v/v methanol in dichloromethane) afforded the product (3, 0.280 g, 26 %). An analytical sample was obtained by recrystallization from methanol. Attempts to improve the yield using different bases (sodium ethylate or potassium carbonate), reaction times or temperatures (0 °C to 100 °C) failed. T.l.c. showed that compound 3 is not indefinitely stable in the reaction mixture. Adenine is known to react with alkylating agents under basic conditions to give N9-substituted derivatives [3].
Yield: 26 %.
Mp.: 187-189 °C (dec.).
IR (KBr): 1334m (νsC=N=N); 1644s; 1658s (νC=O); 2110s (νasC=N=N).
1H NMR (DMSO-d6, 400 MHz): 5.03 (s, 2 H, CH2N); 6.18 (s, 1 H, CHN2); 7.25 (br s, 2 H, NH2); 8.08 (s, 1 H, H-2*); 8.12 (s, 1 H, H-8*).
13C NMR (DMSO-d6, 100 MHz, assignment based on J-modulated spin-echo experiment): 48.98 (CH2N); 53.77 (CHN2); 118.29 (C-5); 141.46 (C-8); 149.68 (C-4); 152.56 (C-2); 155.93 (C-6); 188.43 (CO).
EI-MS (NH4Cl additive, m/z, %): 217 (3, M+); 189 (100, [M-28]+); 160 (23); 148 (18); 135 (48, [adenine]+); 108 (35, [adenine-HCN]+); 55 (80, C3H3O+).
Anal calcd. for C8H7N7O (217.188): C, 44.24; H, 3.25; N, 45.14; found C, 44.06; H, 3.02; N, 45.15 %.

Supplementary materials

Supplementary File 1Supplementary File 2

References

  1. Mashraqui, S. H.; Keehn, P. M. J. Am. Chem. Soc. 1982, 104, 4461–4465. [CrossRef]
  2. Padwa, A.; Austin, D. J.; Precedo, L.; Zhi, L. J. Org. Chem. 1993, 58, 1144–1150. [CrossRef]
  3. Holy, A. Collect. Czech. Chem. Commun. 1982, 47, 2786–2805.
  • Sample availability: sample available from the author.

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MDPI and ACS Style

Kovács, L. 1-(6-Amino-9H-purin-9-yl)-3-diazoacetone. Molecules 2000, 5, M130. https://doi.org/10.3390/M130

AMA Style

Kovács L. 1-(6-Amino-9H-purin-9-yl)-3-diazoacetone. Molecules. 2000; 5(1):M130. https://doi.org/10.3390/M130

Chicago/Turabian Style

Kovács, Lajos. 2000. "1-(6-Amino-9H-purin-9-yl)-3-diazoacetone" Molecules 5, no. 1: M130. https://doi.org/10.3390/M130

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