Benzyl Bromide → HCID 53804992, compound

HRID 1814960Notes

Reaction equation

HRID 1814960 reaction equation
[C:1]([O:4][C@@H:5]([CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[NH:17][C:16]([CH2:21][OH:22])=[N:15][C:14]=2[N:13]([CH3:23])[C:11]1=[O:12])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)C=O>[C:1]([O:4][C@@H:5]([CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:16]([CH2:21][OH:22])=[N:15][C:14]=2[N:13]([CH3:23])[C:11]1=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 54007389HCID 54007389, compound

Product 1

HCID 53804992HCID 53804992, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (5)-1-(5-acetoxyhexyl)-8-hydroxymethyl-3-methylxanthine (prepared as described for synthesis of (R )-1-(5-hydroxyhexyl)-8-aminomethyl-3,7-dimethylxanthine libraries) (10.5 g, 31 mmol) and potassium carbonate (8.6 g, 62 mmol) in dimethylformamide (100 ml) was added benzyl bromide (8.67 g, 39 mmol). After stirring at room temperature overnight, the mixture was poured into ice water (250 ml) and stirred at 0-5° C. for 1 hour. The precipitate was filtered, rinsed with water (4x 50 ml) and dried under vacuum to provide (S)-1-(5-acetoxyhexyl)-7-benzyl-8-hydroxymethyl-3-methylxanthine (9.8 g, 74% yield).

Workup

  1. stirringstirred at 0-5° C. for 1 hour
  2. filtrationThe precipitate was filtered
  3. washrinsed with water (4x 50 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ed6b6115496e43fdaf2b76c062aad72d
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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