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

HRID 133114

반응식

HRID 133114 반응식
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]

참가 물질

8

반응물 4

HCID 190Adenine2회HCID 7303Ethylene carbonateHCID 60172AdefovirHCID 10197750Magnesium dipropan-2-olate

생성물 1

HCID 2426522-(6-Aminopurin-9-yl)ethanol수율 90%

시약·촉매·용매 3

HCID 14798Sodium Hydroxide촉매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-b840640a941c43a098c2c7aeb4126f6d
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390791B2

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