Water → HCID 14632750, compound

HRID 266243Notes

Reaction equation

HRID 266243 reaction equation
[H-].[Li+].[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([NH:8][CH:9]=[N:10]2)=[C:6]([O:13][CH2:14][CH2:15][O:16][CH3:17])[N:5]=1.[CH2:18]([O:20][P:21]([CH2:26][O:27][CH2:28][CH2:29][CH2:30]Br)([O:23][CH2:24][CH3:25])=[O:22])[CH3:19].O>CN(C)C=O>[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[CH2:30][CH2:29][CH2:28][O:27][CH2:26][P:21]([O:23][CH2:24][CH3:25])([O:20][CH2:18][CH3:19])=[O:22])=[C:6]([O:13][CH2:14][CH2:15][O:16][CH3:17])[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 62714Lithium hydrideHCID 135468096-(2-Methoxyethoxy)-7H-purin-2-amineHCID 14411012HCID 14411012, compound

Product 1

HCID 14632750HCID 14632750, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a suspension of lithium hydride (560 mg, 60 mmol) in dry dimethylformamide (DMF, 200 ml) was added 2-amino-6-methoxyethoxy purine (8.0 g, 40 mmol) (prepared according to the literature procedure: J. Kjellberg, M. Liljenberg and N. G. Johansson, Tetrahedron Lett. 877, 1986]and stirred for 60 min at 25° C. To this solution was added over 3 min a solution of 3-(diethylphosphonomethoxy)-1-bromopropane (12.0 g, 41.5 mmol) in DMF (5 mL) and the solution was heated at 55° C. for 4 h. The reaction mixture was then cooled to room temperature and water (50 mL) was added dropwise. Insoluble material was removed by filtration. The filtrate was concentrated in vacuo to give a viscous oil which was purified by column chromatography on silica gel (5% methanol in CH2Cl2) to afford 2-amino-9-(3-(diethylphosphonomethoxy)propyl]-6-methoxyethoxy purine as a white crystalline solid: yield 3.45 g (21%); mp 78°-79° C.

Workup

  1. customprepared
  2. temperaturethe solution was heated at 55° C. for 4 h
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. customInsoluble material was removed by filtration
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give a viscous oil which
  7. customwas purified by column chromatography on silica gel (5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-4fa781b582b541ef8042ceed59564534
Source dataset
uspto-grants-1997_07
Patent number
US05650510

Reaction notes

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