ChemicalBook CAS DataBase List 5-vinyl-2'-deoxyuridine

5-vinyl-2'-deoxyuridine synthesis

10synthesis methods

Product Name:5-vinyl-2'-deoxyuridine
CAS Number:55520-67-7
Molecular formula:C11H14N2O5
Molecular Weight:254.24

54-42-2 Synthesis

54-42-2
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7486-35-3
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55520-67-7
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Yield:55520-67-7 92%

Reaction Conditions:

with tetrakis(triphenylphosphine) palladium⁽⁰⁾ in tetrahydrofuran; for 12 h;Inert atmosphere;Reflux;

Steps:

11 Synthesis of 5-vinyl-2′-deoxyuridine 2:

To a degassed solution of 5-iodo-2′-deoxyuridine 1 (2g, 5.65mmol) and tri-n-butyl(vinyl)stannane (1.82mL, 6.21mmol) in anhydrous THF (50mL) with argon, tetrakis(triphenylphosphine) palladium(0) (0.326g, 0.282mmol) was added; and stirred under reflux for 12h. The reaction mixture was diluted with dichloromethane (150mL) and was filtered through Hyflo Super Cel. The solvents were removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel using 5% ethanol in dichloromethane as eluent to give 5-vinyl-2′-deoxyuridine 2 as a semi white solid (1.32g, 92% yield). Spectral characterization data of compound 2 were in agreement with previously reported literature data.⁶ ¹H NMR (CD₃OD, 400MHz) δ 8.32 (s, 1H), 6.51 (dd, J=17.8Hz, 10.5Hz, 1H), 6.3 (t, J=6.4Hz, 1H), 5.91 (dd, J=17.8Hz, 2.1Hz, 1H), 5.20 (dd, J=10.5Hz, 2.1Hz, 1H), 4.41-4.39 (m, 1H), 3.96-3.93 (m, 3H), 3.82-3.72 (m, 2H), 2.34-2.21 (m, 2H); MS (ESI, m/z): calc. for C₁₁H₁₄N₂O₅ [M+H]⁺: 255.09; found 255.1 [M+H]⁺.

References:

Kore, Anilkumar R.;Yang, Bo;Srinivasan, Balasubramanian [Tetrahedron Letters,2015,vol. 56,# 6,p. 808 - 811]