Dimethylformamide → HCID 15886851, compound

HRID 842719Notes

Reaction equation

HRID 842719 reaction equation
[CH3:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH2:11])[N:3]=1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[CH2:23]([N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([CH3:1])=[N:3][C:4]=2[NH2:11])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 150482-Methyladenine

Product 1

HCID 15886851HCID 15886851, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

70 mg (0.47 mmol) of 2-methyladenine was dissolved in a mixed solvent composed of DMF (15 ml) and water (5 ml). To this solution, 0.26 g (1.88 mmol) of potassium carbonate and 0.5 ml (about 2 mmol) of benzyl bromide were added and stirred at room temperature for 16 hr. After the solvent was removed by vacuum distillation, the residue was extracted with chloroform, dried over anhydrous magnesium sulfate and then concentrated. The resultant residue was purified by column chromatography (eluent:dichloromethane:methanol=50:1-30:1) to thereby obtain 0.12 g of 9-benzyl-2-methyladenine.

Workup

  1. customAfter the solvent was removed by vacuum distillation
  2. extractionthe residue was extracted with chloroform
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant residue was purified by column chromatography (eluent:dichloromethane:methanol=50:1-30:1)

Sources & evidence

ORD record
ord-34c888c20d494bb7bb51cf57a561b731
Source dataset
uspto-grants-2002_04
Patent number
US06376501B1

Reaction notes

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