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

HRID 133114

Reaction equation

HRID 133114 reaction equation
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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-b840640a941c43a098c2c7aeb4126f6d
Source dataset
uspto-grants-2008_06
Patent number
US07390791B2

Linked notes

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