Bromotrimethylsilane → (E)-9-(4-Phosphonobut-3-enyl)adenine

HRID 1708094노트

반응식

HRID 1708094 반응식
C([O:4][P:5](/[CH:11]=[CH:12]/[CH2:13][CH2:14][N:15]1[CH:23]=[N:22][C:21]2[C:16]1=[N:17][CH:18]=[N:19][C:20]=2[NH2:24])([O:7]C(C)C)=[O:6])(C)C.Br[Si](C)(C)C>ClCCl>[P:5](/[CH:11]=[CH:12]/[CH2:13][CH2:14][N:15]1[CH:23]=[N:22][C:21]2[C:16]1=[N:17][CH:18]=[N:19][C:20]=2[NH2:24])([OH:7])([OH:6])=[O:4]

참가 물질

4

반응물 2

HCID 76113BromotrimethylsilaneHCID 10473258(E)-9-[4-(diisopropoxyphosphoryl)but-3-enyl]adenine

생성물 1

HCID 6474311(E)-9-(4-Phosphonobut-3-enyl)adenine수율 81.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (E)-9-[4-(diisopropoxyphosphoryl)but-3-enyl]adenine (111 mg, 314 μmol) in dichloromethane (6 ml) was added bromotrimethylsilane (0.9 g, 6.28 mmol) and the mixture was stirred at room temperature under dry nitrogen for 18 hr. The solution was evaporated to dryness and the residue azeotroped with methanol (×3). The residue was purified by column chromatography on reverse phase silica gel eluting with water to give (E)-9-(4-phosphonobut-3-enyl)adenine as a white solid (69 mg, 81%), m.p. 263°-266° C.; λmax (MeOH) 261 (10,810)nm; υmax (KBr) 3360, 3095, 1685, 1605, 1520, 1415,and 1228 cm-1 ; δH (D2O +one drop of NH4OH solution) 2.63 (2H, m, CH2), 4.31 (2H, t, J 7 Hz, CH2N), 5.72 (1H, pseudo-t, J 17 Hz, PCH =CH), 6.14 (1H, pseudo-tt, J 7 Hz and 17 Hz, PCH=CH), 8.13 (1H, s, H-2/H-8), 8.19 (1H, s, H-2/H-8); FABMS (thioglycerol) 270 (MH+) (Found: C, 37.29; H, 4.38; N, 24.09%. C9H12N5O3P.0.25HBr requires C, 37.35; H, 4.27; N, 24.20%).

후처리

  1. customThe solution was evaporated to dryness
  2. customthe residue azeotroped with methanol (×3)
  3. customThe residue was purified by column chromatography on reverse phase silica gel eluting with water

출처 및 근거

ORD 기록
ord-6a3eaa3b78e24a168b717b4841411fb5
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05356886

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