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

HRID 1708094ノート

反応式

HRID 1708094 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-6a3eaa3b78e24a168b717b4841411fb5
出典データセット
uspto-grants-1994_10
特許番号
US05356886

反応ノート

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