Methylhydrazine → HCID 15747245, compound

HRID 1770340Notes

Reaction equation

[Si:1]([O:18][C@@H:19]1[C@@H:23]([CH2:24][O:25][N:26]2C(=O)C3=CC=CC=C3C2=O)[O:22][C@@H:21]([N:37]2[CH:45]=[C:43]([CH3:44])[C:41](=[O:42])[NH:40][C:38]2=[O:39])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CNN>C(Cl)Cl>[NH2:26][O:25][CH2:24][C@H:23]1[O:22][C@@H:21]([N:37]2[CH:45]=[C:43]([CH3:44])[C:41](=[O:42])[NH:40][C:38]2=[O:39])[CH2:20][C@@H:19]1[O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 3'-O-(t-butyldiphenylsilyl)-5'-O-phthalimidothymidine (10 g, 16 mmol), in dry CH2Cl2 (100 ml) was added methylhydrazine (1.3 ml, 24 mmol) under argon at room temperature and solution stirred for 12 h. The solution was cooled (0° C.) and filtered. The white residue was washed with CH2Cl2 (2×25 ml) and combined filtrates were evaporated to furnish gummy residue. The residue on purification by silica gel column chromatography (elution with CH2Cl2 :MeOH, 98:2, v/v) furnished 7.03 g (89%) of 5'-O-amino-3'-O-(t-butyldiphenylsilyl)thymidine that crystallized from CH2Cl2 /MeOH mp 141°-143° C. 1H NMR (DMSO-d6) δ 11.29 (s, 1, NH), 7.42-7.62 (m, 11, TBDPhH, C6H), 6.25 (dd, 1H1', J1',2' =8.4 Hz, J1',2" 6.3 Hz), 6.02 (s, 2, NH2), 4.35 (m, 1, H4'), 4.04 (m, 1, H3'), 3.34-3.51 (m, 2, H5',5"), 2.04 (m, 2, H2', 2"), 1.73 (s, 3, CH3), 1.03 (s, 9, C(CH3)3).

Workup

filtrationfiltered
washThe white residue was washed with CH2Cl2 (2×25 ml)
customwere evaporated
customto furnish gummy residue
customThe residue on purification by silica gel column chromatography (
washelution with CH2Cl2

Sources & evidence

ORD record: ord-fac0f0e3f38749b1a1b31a1e124ef0b2
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05386023

Reaction notes

Loading…