Triphenylphosphine → N-[4-(2-Amino-8-(3-(tert-butoxycarbonylamino)-propyl)-9H-purin-6-yloxymethyl)-benzyl]-2,2,2-trifluoro-acetamide

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Reaction Steps

Nitroso-pyrimidine 39 (Example 22, 1.84 g, 3.3 mmol) and triphenylphosphine (1.89 g, 7 mmol) in 20 mL o-xylene are heated to reflux for 10 h. After cooling to room temperature the solvent is removed in vacuo and the remaining residue redissolved in ethyl acetate. The residue is adsorbed on SiO2 and purified by flash column chromatography (ethyl acetate/ethanol 1:0 to 10:1) to yield the title compound as a colorless solid (1.04 g, 3.53 mmol, 50.4%). 1H-NMR (400 MHz, DMSO-d6): δ=7.46 (d, J=8.1, 2H, ArH), 7.28 (d, J=8.1, 2H, ArH), 6.85 (t, J=5.3, 1H, CONH), 6.41 (s, 2H, NH2), 5.41 (s, 2H, OCH2), 4.38 (s, 2H, CH2), 2.93 (q, J=6.5, 2H, CH2), 2.60 (t, J=7.1, 2H, CH2), 1.76 (qt, J=7.1; 2H, CH2), 1.35 (s, 9H, (CH3)3) ppm. MS (ESI) m/z 524.3 [M+H]+.

Provenance & Evidence