HCID 135545177, compound → HCID 135404759, compound

HRID 266238Notes

Reaction equation

HRID 266238 reaction equation
C([NH:4][C:5]1[NH:6][C:7](=[O:26])[C:8]2[N:9]=[CH:10][N:11]([CH2:14][CH2:15][O:16][CH2:17][P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])[C:12]=2[N:13]=1)(=O)C>CN.C(OCC)(=O)C>[CH2:24]([O:23][P:18]([CH2:17][O:16][CH2:15][CH2:14][N:11]1[CH:10]=[N:9][C:8]2[C:7](=[O:26])[NH:6][C:5]([NH2:4])=[N:13][C:12]1=2)([O:20][CH2:21][CH3:22])=[O:19])[CH3:25]

Participants

4

Reactant 1

HCID 135545177HCID 135545177, compound

Product 1

HCID 135404759HCID 135404759, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 6329MethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-N-Acetyl-9-(2-(diethylphosphonomethoxy)ethyl)guanine (1.42 g, 3.68 mmol) was dissolved in 50 mL of 40% aqueous methylamine and the solution was stirred at rt for 45 min. The reaction mixture was concentrated in vacuo and evaporated three times with toluene to give a gummy, white solid. The crude material was stirred in hot ethyl acetate for 1 h, then cooled to rt, and the product collected by filtration to provide 1.19 g of 9-(2-(diethylphosphonomethoxy)ethyl)guanine

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customevaporated three times with toluene
  3. customto give a gummy, white solid
  4. temperaturecooled to rt
  5. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-757f6ee2d753470e9b6094dcccb51297
Source dataset
uspto-grants-1997_07
Patent number
US05650510

Reaction notes

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