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

HRID 1708090

Reaktionsgleichung

Reaktionsgleichung von HRID 1708090
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-231965bd897b49bea42107d1e0e69097
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05356886

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