Diethyl Ether → HCID 13747690, compound

HRID 1762546Notes

Reaction equation

HRID 1762546 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][N:6]1[C:14]2[N:13]=[CH:12][N:11]([CH3:15])C=2C(=O)[N:8]([CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:23])[CH3:22])[C:7]1=[O:24].CC[O:27][CH2:28][CH3:29]>>[OH:23][C:21]([CH3:22])([CH2:1][CH3:2])[CH2:20][CH2:19][CH2:18][CH2:17][N:8]1[C:28](=[O:27])[C:29]2[N:11]([CH3:15])[CH:12]=[N:13][C:14]=2[N:6]([CH3:5])[C:7]1=[O:24]

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 4740PentoxifyllineHCID 178418443HCID 178418443, compound

Product 1

HCID 13747690HCID 13747690, compoundYield 81.1%

Procedure

20.0 g (0.15 mol) of ethylmagnesium bromide are taken as a 40% strength solution in ether, and 27.8 g (0.1 mol) of 3,7-dimethyl-1-(5-oxohexyl)-xanthine in 1 liter of dry ether are metered in dropwise at room temperature, while stirring, whereupon a voluminous precipitate forms. The mixture is heated and is subsequently stirred, while boiling gently under reflux, for one hour. It is then worked up as described in the preceding Example 9 to give 25 g of oily crude product (81.1% of theory), which gradually crystallizes completely and is purified by recrystallization from diisopropyl ether, with the addition of a little ethyl acetate, at the boiling point.

Workup

  1. customdropwise at room temperature
  2. temperatureThe mixture is heated
  3. stirringis subsequently stirred
  4. temperatureunder reflux, for one hour

Sources & evidence

ORD record
ord-048f6cc4164347a7b0be9b850ffab820
Source dataset
uspto-grants-1989_05
Patent number
US04833146

Reaction notes

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