1-[(2-Acetoxyethoxy)methyl]-3-allyl-6-azauracil

Smaail Radi^a and Hassan B. Lazrek^b

^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: 90 % (viscous and colourless).

Rf: 0.73 (CHCl₃ / MeOH, 9/1, V/V).

¹H NMR (DMSO-d₆): 2.06 (s, 3H, COOCH₃); 3.75 (m, 2H, OCH₂CH₂O); 4.05 (m, 2H, OCH₂CH₂O); 4.50 (d, 2H, NCH₂); 5.15 (d, 1H, Hcis); 5.25 (s, 2H, OCH₂N); 5.30 (d, 1H, Htrans); 5.90 (m, 1H, CH=C); 7.65 (s, 1H, H⁵).

UV (l max (nm), H₂O): 273.

MS (FAB, m/z): 270 [MH]⁺

Anal. calc. for C₁₁H₁₅N₃O₅: C 49.07, H 5.61, N 15.61; Found: C 49.00, H 5.50, N 15.50.

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 & Nucleotides 1989, 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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