Potassium Carbonate → HCID 20041122, compound

HRID 1762556Notes

Reaction equation

HRID 1762556 reaction equation
[OH:1][CH:2]([CH2:16][OH:17])[CH2:3][N:4]1[C:12]2[C:11](=[O:13])[NH:10][C:9](=[O:14])[N:8]([CH3:15])[C:7]=2[N:6]=[CH:5]1.Cl[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:26])([CH3:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:1][CH:2]([CH2:16][OH:17])[CH2:3][N:4]1[C:12]2[C:11](=[O:13])[N:10]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])[C:9](=[O:14])[N:8]([CH3:15])[C:7]=2[N:6]=[CH:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3616685AC1MUDJSHCID 137476791-Chloro-5-hydroxy-5-methylhexane

Product 1

HCID 20041122HCID 20041122, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 18 g (0.075 mol) of the xanthine compound from stage (a), 12.5 g (0.083mol) of 1-chloro-5-hydroxy-5-methylhexane (Example 1a) and 11.5 g (0.083 mol) of potassium carbonate in 500 ml of dimethylformamide is stirred for 18 hours at 110° C., after which the hot mixture is filtered and the filtrate is concentrated in vacuo. The oily crude product, which gradually crystallizes through, can advantageously be purified by filtration over a silica gel column using a chloroform/methanol (10:1) solvent mixture, followed by a final recrystallization from ethyl acetate with the addition of petroleum ether, at the boil.

Workup

  1. filtrationafter which the hot mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe oily crude product, which gradually crystallizes through,
  4. filtrationcan advantageously be purified by filtration over a silica gel column
  5. customrecrystallization from ethyl acetate
  6. additionwith the addition of petroleum ether

Sources & evidence

ORD record
ord-4c5596507ba14ffba2e2f104168b3061
Source dataset
uspto-grants-1989_05
Patent number
US04833146

Reaction notes

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