1-[(2-Acetoxyethoxy)methyl]-3-methyl-5-bromo-6-azauracil
Smaail Radia and Hassan B. Lazrekb
a Laboratoire de Chimie Organique
Physique, Faculté des Sciences-oujda, Morocco. E-mail: [email protected].
b Laboratoire de Chimie Bio-organique,
Faculté des Sciences-Semlalia, Marrakech, Morocco.
Received: 23 February 2000 / Accepted: 28 February 2000 / Published: 28 April 2000
The product 2 was prepared via a direct condensation under solid-liquid phase transfer catalysis (S.L.P.T.C.) [1] conditions. To a solution of 0.02 mmole of tetraglyme in 4 ml of anhydrous THF, 0.11 mmole of potassium tert-butoxide is added. Then 0.1 mmole of the acyclonucleoside 1 [2] is added, the reaction mixture is stirred at room temperature for 15 min. The reaction mixture is cooled to 0°C and 0.11 mmole of alkylating agent in 2 ml of dry THF is added dropwise with stirring. When the addition is finished, the reaction mixture is stirred at 0°C for 30 min. The reaction mixture is then filtered and the filtrate is evaporated in vacuo to dryness. The residue is then chromatographed on a silica gel column and the expected acyclonucleoside 2 was isolated. Yield: 80 % (viscous and colourless)
Rf: 0.63 (CHCl3 / MeOH, 9/1, V/V).
1H NMR (DMSO-d6): 2.00 (s, 3H, COOCH3); 3.60 (s, 3H, CH3); 3.70 (m, 2H, OCH2CH2O); 4.10 (m, 2H, OCH2CH2O); 5.25 (s, 2H, OCH2N).
UV (l max (nm), H2O): 288.
MS (m/z): 321 [M (79Br)]+, 323 [M (81Br)]+
Anal. calc. for C9H12BrN3O5: C 33.55, H 3.75, N 13.04; Found: C 33.54, H 3.75, N 12.75.
References
1. | Lazrek, H. B.; Taourirte, M.; Barascut, J. L.; Imbach, J. L. Nucleosides & Nucleotides 1991, 10, 1285-1293. |
2. | Purkayastha, S.; Lazrek, H. B.; Panzica, R. P.; Naguib, F. N. M.; El-Kouni, M. H. Nucleosides & Nucleotides1989, 8, 349-356. |
Acknowledgement: This work was supported by the C.N.R. (Marocco), the Deutsche Forschungsgemeinschaft and the University of Konstanz (Germany).
Sample Availability: Available from the authors.
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