Potassium Carbonate → 1-[2-(2-Nitrophenyl)-2-oxoethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-chloroxanthine

HRID 1174567Notes

Reaction equation

HRID 1174567 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([Cl:11])[N:7]([CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[C:6]=2[C:5](=[O:17])[NH:4][C:3]1=[O:18].Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N+:29]([O-:31])=[O:30])=[O:22].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN(C)C=O>[N+:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:21](=[O:22])[CH2:20][N:4]1[C:5](=[O:17])[C:6]2[N:7]([CH2:12][CH:13]=[C:14]([CH3:15])[CH3:16])[C:8]([Cl:11])=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:18])([O-:31])=[O:30]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 2440252-Bromo-2'-nitroacetophenoneHCID 220297223-Methyl-7-(3-methyl-2-buten-1-yl)-8-chloro-xanthine

Product 1

HCID 179648741-[2-(2-Nitrophenyl)-2-oxoethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-chloroxanthine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6.02 g of 3-methyl-7-(3-methyl-2-buten-1-yl)-8-chloroxanthine, 5.86 g of 2-bromo-1-(2-nitrophenyl)ethanone, and 5.00 g of potassium carbonate in 150 mL of NAN-dimethylformamide is stirred for approximately 26 hours at 60° C. For working up, the cooled reaction mixture is poured onto a mixture of 500 mL of 1 N sodium hydroxide solution and 200 g of ice. The precipitate formed is suction filtered and dried. Yield: 6.32 g (65% of theory); Rf value: 0.50 (silica gel, cyclohexane/ethyl acetate (4:6)); mass spectrum (ESI+): m/z=432, 434 [M+H]+.

Workup

  1. customthe cooled reaction mixture
  2. customThe precipitate formed
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-b1781616e55a47b4b36b920c66179720
Source dataset
uspto-grants-2010_11
Patent number
US07838529B2

Reaction notes

Loading…