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4.7.4 General Procedure for the preparation of 2-AI-T.
Cool the suspension of hydrazine hydride (2 equiv), in ethanol (0.8 ml.). To the
suspension were added Cu(OAc)2 (5 mol %) in water (0.2 ml). and stirred it for 2 min
at 0 o C. To this were added acetylene (1.5 eq) and hydroxyl salt (1 eq.) The reaction
mixture was irradiated at 100 0 o C at the maximum power 35 W for 2-5 min. After
completion of the reaction, the solvent was removed under reduce pressure. The crude
product was purifier by column chromatography over silica gel using DCM /
methanol / 7N methanolic NH3 (96:3:1) as the eluent.
4.8 Spectral Characterization
2-Azidoethanamine (BS-167)
H 2N
Yield: 41 %. 1 H NMR (300 MHz, CDCl3): δ = 3.37 (t, J = 5.61 Hz, 2H), 2.88 (t, J =
5.50 Hz, 2H), 1.53 (Br s, 2H).
3-Azidopropan-1-amine (BS-220)
H 2N
Yield: 45 %. 1 H NMR (300 MHz, CDCl3): δ = 3.38 (t, J = 6.93 Hz, 2H), 2.81 (t, J =
6.84 Hz, 2H), 1.73 (m, 2H), 1.36 (Br s, 2H).
N-(2-Azidoethyl)pyrimidin-2-amine (BS-168)
N
N
N
H
Yield: 67 %. 1 H NMR (300 MHz, CDCl3): δ = 8.30 (d, J = 4.74 Hz, 2H), 6.58 (t, J =
4.74 Hz, 1H), 5.44 (Br s, 1H), 3.64 (m, 2H), 3.54 (t, J = 5.58 Hz, 2H), 13 C NMR
(75.5 MHz, CDCl3): δ =162.0, 158.1, 158.0, 111.1, 50.8, 40.7. HRMS (EI) C6H6N6,
calcd 164.0810, found :.
N-(3-Azidopropyl)pyrimidin-2-amine (BS-221)
N
N
N
H
N 3
N 3
N 3
N 3