Methylhydrazine → HCID 10088675, compound

HRID 1708099Notes

Reaction equation

HRID 1708099 reaction equation
[CH2:1]([O:3][P:4](/[CH:9]=[CH:10]\[CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[N:23]1C(=O)C2=CC=CC=C2C1=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].CNN>C(O)C>[CH2:7]([O:6][P:4](/[CH:9]=[CH:10]\[CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[NH2:23])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 11754512(Z)-9-[4-(diethoxyphosphoryl)but-3-enyloxy]-6-phthalimidopurine

Product 1

HCID 10088675HCID 10088675, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (Z)-9-[4-(diethoxyphosphoryl)but-3-enyloxy]-6-phthalimidopurine (305 mg, 647 mmol) and methylhydrazine (31.3 mg, 679 μmol) in ethanol (7 ml) was stirred at room temperature for 1.5 hr. The solvent was removed and the residue was purified by column chromatography on silica gel eluting with dichloromethane-methanol (19:1, 9:1) to afford (Z)-9-[4-(diethoxyphosphoryl)but-3-enyloxy]adenine as a colourless gum (177 mg, 80%); λmax (EtOH) 260 (13,045) nm; υmax (KBr) 3320, 3175, 2980, 1645, 1595, 1325, 1295 and 1240 cm-1 ; δH [(CD3)2SO] 1.22 (6H, t, J 7 Hz, CH3), 2.95 (2H, m, CH2), 3.97 (4H, pseudo qu, J 7 Hz, CH2CH3), 4.46 (2H, t, CH2O ), 5.85 (1H, dd, J 14 Hz and 20 Hz, PCH=CH), 6.65 (1H, ddt, J 7 Hz, 14 Hz and 52Hz, PCH=CH), 7.38 (2H, br.s, NH2), 8.15 (1H, s, H-2/H-8), 8.41 (1H, s, H-2/H-8) (Found: C, 45.30; H, 5.92; N, 20.17%; M+ 341.1253. C13H20N5O4P. 0.3H2O requires C, 45.03; H, 5.96; N, 20.20%; M+ 341.1253).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane-methanol (19:1, 9:1)

Sources & evidence

ORD record
ord-b91ce1321602413caaf58ee4ec4887f8
Source dataset
uspto-grants-1994_10
Patent number
US05356886

Reaction notes

Loading…