Methylhydrazine → (E)-9-[4-(diisopropoxyphosphoryl)but-3-enyloxy]adenine

HRID 1708090

Reaction equation

HRID 1708090 reaction equation
[CH:1]([O:4][P:5](/[CH:11]=[CH:12]/[CH2:13][CH2:14][O:15][N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[N:25]1C(=O)C2=CC=CC=C2C1=O)([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])([CH3:3])[CH3:2].CNN>C(O)C>[CH:8]([O:7][P:5](/[CH:11]=[CH:12]/[CH2:13][CH2:14][O:15][N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH2:25])([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])([CH3:9])[CH3:10]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 10255381(E)-9-[4-(diisopropoxyphosphoryl)but-3-enyloxy]-6-phthalimidopurine

Product 1

HCID 10067662(E)-9-[4-(diisopropoxyphosphoryl)but-3-enyloxy]adenineYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (E)-9-[4-(Diisopropoxyphosphoryl)but-3-enyloxy]-6-phthalimidopurine (186 mg, 370 μmol) and methylhydrazine (18 mg, 390 μmol) in ethanol (4 ml) was stirred at room temperature for 1.5 hr. The solvent was removed and the residue purified by column chromatography on silica gel eluting with dichloromethane-methanol (4:1) to afford (E)-9-[4-(diisopropoxyphosphoryl)but-3-enyloxy]-adenine as a gum (120 mg, 88%); λmax (EtOH) 260 (12,860)nm; υmax (film) 3310, 3170, 2970, 1640, 1590, 1290, 1230 and 980 cm-1 ; δH [(CD3)2SO] 1.26 (12H, pseudo t, J 6 Hz, CH(CH3)2), 2.67 (2H, m, CH2), 4.50 (4H, m, CH2O and CH(CH3)2), 6.05 (1H, dd, J 17 Hz and 22 Hz, PCH=CH), 6.70 (1H, ddt, J 6 Hz, 17 Hz and 22 Hz, PCH=CH), 7.38 (2H, br.s, NH2), 8.14 (1H, s, H-2/H-8), 8.36 (1H, s, H-2/H-8) (Found: M+ 369.1568. C15H24N5O4P requires M+ 369 1566).

Workup

  1. customThe solvent was removed
  2. customthe residue purified by column chromatography on silica gel eluting with dichloromethane-methanol (4:1)

Sources & evidence

ORD record
ord-231965bd897b49bea42107d1e0e69097
Source dataset
uspto-grants-1994_10
Patent number
US05356886

Linked notes

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