Water → 3-Methyl-7-(3-methyl-2-buten-1-yl)-8-chloro-xanthine

HRID 1174568Notes

Reaction equation

HRID 1174568 reaction equation
Br[CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5].[CH3:7][N:8]1[C:16]2[N:15]=[C:14]([Cl:17])[NH:13][C:12]=2[C:11](=[O:18])[NH:10][C:9]1=[O:19].CCN(C(C)C)C(C)C.O>CN(C)C=O>[CH3:7][N:8]1[C:16]2[N:15]=[C:14]([Cl:17])[N:13]([CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5])[C:12]=2[C:11](=[O:18])[NH:10][C:9]1=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 700922-Butene, 1-bromo-3-methyl-HCID 81531DiisopropylethylamineHCID 126175848-chloro-3-methyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

Product 1

HCID 220297223-Methyl-7-(3-methyl-2-buten-1-yl)-8-chloro-xanthine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.87 mL of 1-bromo-3-methyl-2-butene is added to 10.56 g of 3-methyl-8-chloroxanthine and 17 mL of Hünig base in 100 mL of N,N-dimethylformamide. The reaction mixture is stirred for approximately 10 minutes at ambient temperature and then combined with 800 mL of water. The light-colored precipitate formed is suction filtered, washed with ethanol and diethyl ether and dried. Yield: 10.56 g (81% of theory); mass spectrum (ESI+): m/z=269, 271 [M+H]+.

Workup

  1. customThe light-colored precipitate formed
  2. filtrationfiltered
  3. washwashed with ethanol and diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-6818f3ffc96e45e1b528163d03d08076
Source dataset
uspto-grants-2010_11
Patent number
US07838529B2

Reaction notes

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