Adenine → 2-(6-Aminopurin-9-yl)ethanol

HRID 133114

反応式

HRID 133114 の反応式
N1C(N)=C2C(N=CN2)=NC=1.[CH:11]1[N:16]=[C:15]([NH2:17])[C:14]2[N:18]=[CH:19][N:20]([CH2:21][CH2:22][O:23]CP(O)(O)=O)[C:13]=2[N:12]=1.CC(C)[O-].[Mg+2].CC(C)[O-].C1(=O)OCCO1>CN(C=O)C.[OH-].[Na+].C1(C)C=CC=CC=1>[OH:23][CH2:22][CH2:21][N:20]1[CH:19]=[N:18][C:14]2[C:13]1=[N:12][CH:11]=[N:16][C:15]=2[NH2:17]

参加物

8

反応物 4

HCID 190Adenine2 回HCID 7303Ethylene carbonateHCID 60172AdefovirHCID 10197750Magnesium dipropan-2-olate

生成物 1

HCID 2426522-(6-Aminopurin-9-yl)ethanol収率 90%

試薬・触媒・溶媒 3

HCID 14798Sodium Hydroxide触媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

Adenine to PMEA using Magnesium Isopropoxide. To a suspension of adenine (16.8 g, 0.124 mol) in DMF (41.9 ml) was added ethylene carbonate (12.1 g, 0.137 mol) and sodium hydroxide (.100 g, 0.0025 mol). The mixture was heated at 130° C. overnight. The reaction was cooled to below 50° C. and toluene (62.1 ml) was added. The slurry was further cooled to 5° C. for 2 hours, filtered, and rinsed with toluene (2×). The wet solid was dried in vacuo at 65° C. to yield 20.0 g (90%) of 9-(2-hydroxyethyl)adenine as an off-white solid. Mp: 238-240° C.

後処理

  1. temperatureThe reaction was cooled to below 50° C.
  2. temperatureThe slurry was further cooled to 5° C. for 2 hours
  3. filtrationfiltered
  4. washrinsed with toluene (2×)
  5. customThe wet solid was dried in vacuo at 65° C.

出典と根拠

ORDレコード
ord-b840640a941c43a098c2c7aeb4126f6d
出典データセット
uspto-grants-2008_06
特許番号
US07390791B2

関連ノート

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