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

HRID 1708090

반응식

HRID 1708090 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-231965bd897b49bea42107d1e0e69097
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05356886

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