Adenine → 9-Methyladenine

HRID 1509954Notes

Reaction equation

HRID 1509954 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[F-].[CH2:12]([N+](CCCC)(CCCC)CCCC)CCC.CI>O1CCCC1>[CH3:12][N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10]

Participants

5

Reactant 3

HCID 190AdenineHCID 6328Methyl iodideHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 696899-Methyladenine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Adenine (2.0 g, 14.8 mmol), tetrahydrofuran (100 mL) and tetrabutyl-ammonium-fluoride solution in 1.0 M tetrahydrofuran (37 mL, 37 mmol) were added in 300 mL mad apple-type flask with a magnetic stirrer. Methyl-iodide (2.72 mL) added drop wise to the solution in 10 minutes during stirring and allowed to stir for 2.5 hr. The reaction solution was evaporated under reduced pressure. The residues were dissolved in methanol and filtered. The filtrate was added ethanol-water mixture. The object was recrystallized in ethanol-water mixture to give white solids (1.0 g, yield, 45%). 1H NMR (400 MHz, DMSO-d6): δ 3.70 (s, 3H), 7.15 (br, 2H), 8.07 (s, 1H), 8.13 (s, 1H), 13C NMR (100 MHz, DMSO-d6): δ 29.3, 118.6, 141.3, 149.8, 152.4, 155.9; MS (ESI+)calcd for C6H7N5+(M+H+) 150.0774, found 150.0914.

Workup

  1. stirringto stir for 2.5 hr
  2. customThe reaction solution was evaporated under reduced pressure
  3. dissolutionThe residues were dissolved in methanol
  4. filtrationfiltered
  5. additionThe filtrate was added ethanol-water mixture
  6. customThe object was recrystallized in ethanol-water mixture
  7. customto give white
  8. customsolids (1.0 g, yield, 45%)

Sources & evidence

ORD record
ord-a0ece9514e714439b2902ebc32ad3dc6
Source dataset
uspto-grants-2012_07
Patent number
US08211899B2

Reaction notes

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