Benzyl Bromide → 7-Benzyl-3-methylxanthine

HRID 1792035Notes

Reaction equation

HRID 1792035 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:19]([N:7]1[C:6]2[C:5](=[O:11])[NH:4][C:3](=[O:12])[N:2]([CH3:1])[C:10]=2[N:9]=[CH:8]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 706393-Methylxanthine

Product 1

HCID 6856307-Benzyl-3-methylxanthine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methylxanthine (2.882 g) was suspended in N,N-dimethylformamide (40 ml), and potassium carbonate (3 g) and benzyl bromide (2.5 ml) was added thereto. The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate, and washed with 1 N hydrochloric acid. The deposited crystals were collected by filtration and washed with ethyl acetate to give 3.18 g of the title compound.

Workup

  1. washwashed with 1 N hydrochloric acid
  2. filtrationThe deposited crystals were collected by filtration
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-af1959f7521043bca05950b1fe807b59
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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