Dimethylformamide → 9-(2-Acetoxyethoxymethyl)guanine

HRID 2198928Notes

Reaction equation

HRID 2198928 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2.CN(C)C=O.[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1>[C:22]([O:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 135398513Acyclovir

Product 1

HCID 1354469309-(2-Acetoxyethoxymethyl)guanine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 9-(2-hydroxyethoxymethyl)guanine (4.6 g), dry dimethylformamide (46 ml), acetic anhydride (16 ml) and dry pyridine (24 ml) was stirred at room temperature overnight. The resulting white solid was removed by filtration and dissolved in warm dimethylformamide (100 ml), pyridine (10 ml) and acetic anhydride (8 ml) added and the mixture stirred for 18 hr. The white solid formed was removed by filtration, washed with ethyl acetate and recrystallized from dimethylformamide to give 9-(2-acetyloxyethoxymethyl)guanine (3.3 g), m.p. 240°-241° C.

Workup

  1. customThe resulting white solid was removed by filtration
  2. dissolutiondissolved in warm dimethylformamide (100 ml)
  3. additionpyridine (10 ml) and acetic anhydride (8 ml) added
  4. stirringthe mixture stirred for 18 hr
  5. customThe white solid formed
  6. customwas removed by filtration
  7. washwashed with ethyl acetate
  8. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-0f0bd56a3d0f4554ac6faf93825c4388
Source dataset
uspto-grants-1982_11
Patent number
US04360522

Reaction notes

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