BenzaMide, N-[1,2-dihydro-1-(2-C-Methyl-β-D-arabinofuranosyl)-2-oxo-4-pyriMidinyl]- synthesis

7synthesis methods

Product Name:BenzaMide, N-[1,2-dihydro-1-(2-C-Methyl-β-D-arabinofuranosyl)-2-oxo-4-pyriMidinyl]-
CAS Number:817204-35-6
Molecular formula:C17H19N3O6
Molecular Weight:361.3493

917-54-4
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119411-03-9 Synthesis

Cytidine, N-benzoyl-2^-deoxy-2^-oxo-3^,5^-O-[1,1,3,3-tetrakis(1-Methylethyl)-1,3-disiloxanediyl]-

119411-03-9
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BenzaMide, N-[1,2-dihydro-1-(2-C-Methyl-β-D-arabinofuranosyl)-2-oxo-4-pyriMidinyl]-

817204-35-6
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Yield:817204-35-6 53%

Reaction Conditions:

in diethyl ether at -78; for 2 h;Inert atmosphere;

Steps:

7.c c. Preparation of compound 703.

c. Preparation of compound 703. Compound 702 (48.57 g, 8.26 mmol) was dissolved in anhydrous toluene (~400 mL) and the solvent was removed in vacuo with exclusion of moisture. The residue was then further dried in vacuo (oil pump) for another 2 hours. With strict exclusion of moisture, the residual foam was dissolved in anhydrous diethyl ether (1.03 L) under argon. The resulting solution was cooled to -78°C under argon and MeLi (1.6 M, 258.0 mL, 0.413 mol) was added dropwise via additional funnel. After the addition was complete, the mixture was stirred for 2 hours at -78°C. Aqueous 1 M NH₄CI (500 mL) was added slowly. After warming to room temperature, the mixture was washed with H₂0 (2 x 500 mL), dried (Na₂S0₄), and then concentrated to dryness to give a brown foam (-60 g, >100%). The reaction was performed two more times using 37.62 g and 56.4 g of compound 702. The combined crude products (128.0 g, 0.212 mol) were dissolved in THF (1.28 L) and treated with coned HOAc (23 mL, 0.402 mol). To the solution was added TBAF (384.0 mL, 1 M in THF). The solution was stirred at room temperature for 0.75 hours and the mixture was treated with silica gel (750 g) and concentrated to dryness. The powder was placed on a silica gel column packed in CH₂CI₂. Elution with 1 :7 EtOH-CH₂CI₂ afforded a dark waxy solid that was pre-adsorbed on silica gel (300 g) and chromatographed as before. Compound 703 (46.4 g, 53.0 % from 702) was isolated as an off-white solid. ¹H NMR (DMSO-d₆): δ 1.20 (s, 3H, CH₃), 3.62-3.69 (m, 2H,), 3.73-3.78 (m, 2H,), 5.19 (t, 1H, J = 5.4 Hz, OH-5'), 5.25 (s, 1 H, OH-2'), 5.52 (d, 1 H, J = 5.0 Hz, OH-3'), 5.99 (s, 1 H, H-1 '), 7.32 (d, 1 H, J = 5.8 Hz), 7.50 (Ψ, 2H, J =7.7 Hz), 7.62 (Ψ, 1 H, J =7.3 Hz), 8.00 (d, 2H, J =7.3 Hz), 8.14 (d, 1H, J =6.9 Hz), 11.22 (s, 1 H, NH). Anal. Calcd for C₁₇H₁₉N₃0₆ · 0.5 H20: C, 55.13; H, 5.44; N, 11.35. Found: C, 55.21 ; H, 5.47; N, 11.33.