1,1-Dimethylhydrazine → 1-Propyl-3-benzyl-8-(1,4benzodioxan-6-yl)xanthine

HRID 1682107Notes

Reaction equation

HRID 1682107 reaction equation
[CH2:1]([N:8]1[C:15]([NH2:16])=[C:14]([N:17]=O)[C:12](=[O:13])[N:11]([CH2:19][CH2:20][CH3:21])[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:22]1[C:27]2[CH:28]=[CH:29][C:30]([CH:32]=O)=[CH:31][C:26]=2[O:25][CH2:24][CH2:23]1.CN(C)N>CN(C)C=O>[CH2:19]([N:11]1[C:12](=[O:13])[C:14]2[NH:17][C:32]([C:30]3[CH:29]=[CH:28][C:27]4[O:22][CH2:23][CH2:24][O:25][C:26]=4[CH:31]=3)=[N:16][C:15]=2[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1=[O:10])[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 59761,1-DimethylhydrazineHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 11254741HCID 11254741, compound

Product 1

HCID 214672231-Propyl-3-benzyl-8-(1,4benzodioxan-6-yl)xanthineYield 23.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.9 g (0.01 mol) of 1-benzyl-3-propyl-5-nitroso-6-aminouracil are added to 60 ml of dimethylformamide together with 2.3 g (0.014 mol) of 1,4-benzodioxan-6-aldehyde, then 0.5 g (0.014 mol) of 1,1-dimethylhydrazine are added and the mixture is refluxed for 8 hours. After working up in the usual way, the crystalline residue is triturated with ethanol and filtered under suction. 1.0 g of the title compound is obtained in the form of yellow crystals, m.p. 290° C.

Workup

  1. temperaturethe mixture is refluxed for 8 hours
  2. customthe crystalline residue is triturated with ethanol
  3. filtrationfiltered under suction

Sources & evidence

ORD record
ord-7fe564dc5f6c47f6b1ddb7cb916247ce
Source dataset
uspto-grants-1992_12
Patent number
US05175291

Reaction notes

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