Methylhydrazine → 3'-O-Amino-5'-O-(t-Butyldimethylsilyl)thymidine

Participants

Reaction Steps

Cold methylhydrazine (1.6 ml, 30 mmol) was added to a stirred solution of 5'-O-(t-butyldimethylsilyl)-3'-O-phthalimidothymidine (2, 4.6 g, 9.18 mmol) in dry CH2Cl2 (60 ml) at 5°-10° C. After 10 minutes white precipitation of 1,2-dihydro-4-hydroxy-2-methyl-1-oxophthalizine occurred. The suspension was stirred at room temperature for 1 h. The suspension was filtered and precipitate washed with CH2Cl2 (2×20 ml). The combined filtrates were concentrated and the residue purified by silica gel column chromatography. Elution with CH2Cl2 :MeOH (100:0→97:3, v/v) furnished the title compound (3.40 g, 100%) as white solid. Crystallization from CH2Cl2 gave white needles, m.p. 171° C.; 1H NMR (CDCl3) δ 0.05 [s, 6, (CH3)2 ], 0.90 [s, 9, (CH3)3, 2.22-2.58 (2m, 2, 2'CH2), 3.9-4.08 (m, 3, 5'CH2, and 3'H) 4.30 (m, 1, 4'H) 5.5 (br s, 2, NH2) 6.2 (m, 1, 1'H) 7.45 (s, 1, C6H) 8.9 (br s, 1, NH). Anal. Calcd. for C16H29N3O5Si: C, 51.72; H, 7.87; N, 11.32. found: C, 51.87, H, 7.81; N, 11.32.

Provenance & Evidence