Methanol → 2-[(6-aminopurin-9-yl)methoxy]ethylphosphonic Acid

HRID 3085ノート

反応式

HRID 3085 の反応式
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]([CH2:11][O:12][CH2:13][CH2:14][P:15](=[O:20])([O-:19])[O:16]CC)[CH:6]=[N:7]2)=[N:3][CH:2]=1.[NH4+].CO.O>CN(C=O)C>[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]([CH2:11][O:12][CH2:13][CH2:14][P:15](=[O:16])([OH:19])[OH:20])[CH:6]=[N:7]2)=[N:3][CH:2]=1

参加物

5

反応物 3

HCID 887MethanolHCID 962WaterHCID 44361146HCID 44361146、化合物

生成物 1

HCID 107786252-[(6-aminopurin-9-yl)methoxy]ethylphosphonic Acid収率 45%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

To a solution of 12 (0.32 g, 1.0 mmol) in DMF (7.0 mL) was added Me3 SiBr (1.07 g, 7.01 mmol). After the solution was stirred at 40° C. for 6 h, a mixture of MeOH and H2O(5:1, 20 mL) was added and the solvents were evaporated. The crude residue was purified by use of column chromatography (resin XAD-4, H2O) to afford 13 (0.12 g, 45%): mp 296° C. (dec.); TLC Rf 0.32 (MeOH); UV λmax (EtOH): 259 nm (ε13 700); 1H NMR(DMSO-d6 /D2O): δ1.49 (m, 2 H, CH2P), 3.80 (m, 2 H, CH2O), 5.55 (s, 2 H, OCH2 N), 7.90, 8.19 (2 s, 2 H, HC(2)+HC(8)). Anal. (C8H12N5 O4P) C, H, N.

後処理

  1. additionwas added
  2. customthe solvents were evaporated
  3. customThe crude residue was purified by use of column chromatography (resin XAD-4, H2O)

出典と根拠

ORDレコード
ord-665b5ee29c834289ad987373eaa9f519
出典データセット
uspto-grants-1998_03
特許番号
US05733890

反応ノート

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