Adenine → 2-Methyladenine

HRID 2399618Notes

Reaction equation

HRID 2399618 reaction equation
[H-].[Na+].[N:3]1[C:11]([NH2:12])=[C:10]2[C:6]([N:7]=[CH:8][NH:9]2)=[N:5][CH:4]=1.[CH3:13]CCCCC>CN(C)C=O>[CH3:13][C:4]1[N:5]=[C:6]2[C:10]([NH:9][CH:8]=[N:7]2)=[C:11]([NH2:12])[N:3]=1

Participants

5

Reactant 3

HCID 190AdenineHCID 8058HexaneHCID 24758Sodium hydride

Product 1

HCID 150482-Methyladenine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 114 mg (2.85 mmol) of 60% sodium hydride (previously washed with hexane) in 18 ml of anhydrous dimethylformamide 386 mg (2.85 mmol) of adenine was added, and the mixture was stirred for 20 minutes at room temperature. Then, 1.18 g (2.38 mmol) of (Z)-[1,2-bis(benzoyloxymethyl)] cyclopropylmethyl p-toluenesulfonate obtained in Example 1 in 6 ml of anhydrous dimethylformamide was added and the mixture was stirred for 3 hours at 60° C. The solvent was distilled off, and dichloromethane and a saturated aqueous solution of sodium bicarbonate was added to the residue. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The resulting residue was subjected to silica gel chromatography (4-10% methanol/dichloromethane) to get 844 mg (1.84 mmol, 77%) of (±)9-[1'α, 2'β-bis-(benzoyloxy methyl) cyclopropan-1'β-yl] methyladenine and 52.8 mg (0.115 mmol), 5 %) of (±)7-[1'α2'β-bis-(benzoyloxymethyl) cyclopropan-1'β-yl] methyladenine.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 3 hours at 60° C
  3. distillationThe solvent was distilled off
  4. additiondichloromethane and a saturated aqueous solution of sodium bicarbonate was added to the residue
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-fe063aef1cef4aa6933671a321af0b7b
Source dataset
uspto-grants-1995_09
Patent number
US05449840

Reaction notes

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