Methyl iodide → HCID 135754930, compound

HRID 1380036Notes

Reaction equation

HRID 1380036 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.[CH3:17][I:18]>CN(C=O)C>[I-:18].[CH3:17][N:13]1[C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]=2[N:6]([CH2:5][O:4][CH2:3][CH2:2][OH:1])[CH2:14]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 135398513Acyclovir

Product 1

HCID 135754930HCID 135754930, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
57 °C

Procedure

To a stirred solution of 9-(2-hydroxyethoxymethyl)guanine (1.0 g; 4.44 mmol) in dry DMF (50 ml) was added a solution of methyl iodide (680 mg, 4.77 mmol) in dry DMF (2 ml). This mixture was heated under a reflux condenser under N2 at 57° C. overnight. The mixture was concentrated in vacuo to an oil and the evaporation was repeated several times from MeOH. The residue was dissolved in MeOH (20 ml) and 2-propanol (150 ml) was added and the mixture was stirred overnight. A yellow solid was obtained which was filtered off (200 mg). This was recrystallized from MeOH (25 ml) (solution filtered through a little charcoal). Crystallization was induced by concentration of the solution, cooling and by the addition of a little 2-propanol.

Workup

  1. concentrationThe mixture was concentrated in vacuo to an oil
  2. customthe evaporation
  3. dissolutionThe residue was dissolved in MeOH (20 ml)
  4. addition2-propanol (150 ml) was added
  5. customA yellow solid was obtained which
  6. filtrationwas filtered off (200 mg)
  7. customThis was recrystallized from MeOH (25 ml) (solution
  8. filtrationfiltered through a little charcoal)
  9. customCrystallization
  10. temperaturecooling and by the addition of a little 2-propanol

Sources & evidence

ORD record
ord-36bcc96d981b42a0bc9f15cecbbe175a
Source dataset
uspto-grants-1986_04
Patent number
US04579849

Reaction notes

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