Methylhydrazine → HCID 15747245, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 5'-O-phthalimido-3'-O-tert-butyl(diphenyl)silylthymidine in dry CH2Cl2 (10 ml) was added methylhydrazine (3 mmol) under anhydrous conditions at room temperature. The solution was stirred for 12 hrs, cooled (0° C.) and filtered. The precipitate was washed with CH2Cl2 (2×10 ml) and combined filtrates were concentrated. The residue was purified by flash column chromatography (silica gel, 20 g). Elution with CH2Cl2 :MeOH (9:1, v/v) furnished the desired 5'-O-amino-3'-O-tert-butyl(diphenyl)silylthymidine as a crystalline product (65%): 1H NMR (CDCl3) δ1.0 (s, 9, C(CH3)3), 1.80 (s, 3, CH3), 1.81 and 2.24 (2 m, 2, C2, CH2), 3.25 and 3.60 (2 m, 2, C5, CH2), 4.0 (m, 1, C3, H), 4.25 (m, 1, C4, H), 5.4 (v br, s, NH2), 6.25 (t, 1, C1, H), 7.2 (s, 1, C6H), 7.25-7.60 (m, 10, ArH), 8.4 (br s, 1, NH).

Provenance & Evidence