Bromotrimethylsilane → 9-(2-(Phosphonomethoxy)ethoxy)adenine

HRID 6260

반응식

HRID 6260 반응식
C([O:3][P:4]([CH2:9][O:10][CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[NH2:23])([O:6]CC)=[O:5])C.C[Si](Br)(C)C>ClCCl>[P:4]([CH2:9][O:10][CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[NH2:23])([OH:6])([OH:5])=[O:3]

참가 물질

4

반응물 2

HCID 76113BromotrimethylsilaneHCID 100431699-[2-(Diethoxyphosphorylmethoxy)ethoxy]adenine

생성물 1

HCID 4731399-(2-(Phosphonomethoxy)ethoxy)adenine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 9-[2-(diethoxyphosphorylmethoxy)ethoxy]adenine (0.63 g, 1.83 mmol) in dry dichloromethane (10 ml) was added trimethylsilyl bromide (1.45 ml, 11 mmol) and the solution stirred at ambient temperature for 2 hours. The solvent was removed under reduced pressure and the residue dissolved in methanol (10 ml). The solvent was evaporated and the residue again dissolved in methanol and solvent evaporated to give a solid residue. Crystallisation from methanol: acetone gave the title compound which was recrystallised from methanol: water (0.24 g, 45%), m.p. 241°-244° C. UV: λmax (EtOH) 259 nm (ε 13,500); IR: νmax (KBr) 3428, 3312, 3084, 1685, 1644, 1612, 1484, 1462, 1455, 1336, 1294, 1278, 1255, 1215, 1195, 1104, 1060, 1046, 1033, 955, 934, 892 cm-1. 1H NMR: δH [(CD3)2SO]3.64 (2H,d,J=8.2 Hz, OCH2P), 3.82 (2H,m,N-OCH2CH2O), 4.50 (2H,m, N-OCH2CH2), 7.42 (2H, br.s, D2O exchangeable NH2), 8.15 (1H,s,H-8), 8.38 (1H,s,H-2) 10.0-4.5 (2H,broad, D2O exchangeable PO(OH )2). Found: C,32.84; H,4.41; N: 23.74%. C8H12N5O5P. H2O requires: C,33.01; H,4.19; N:24.06%.

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in methanol (10 ml)
  3. customThe solvent was evaporated
  4. dissolutionthe residue again dissolved in methanol
  5. customsolvent evaporated
  6. customto give a solid residue
  7. customCrystallisation from methanol

출처 및 근거

ORD 기록
ord-5ee968f7cd244e5c82b70d125ecc7106
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05247085

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