Water → 4(1H)-Pyrimidinone, 2-(((2-(dimethylamino)phenyl)methyl)thio)-6-methyl-

HRID 2247847Notes

Reaction equation

HRID 2247847 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[S:8])[NH:5][C:4](=[O:9])[CH:3]=1.[Cl-].Cl[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH+:19]([CH3:21])[CH3:20].O.[OH-].[Na+]>CS(C)=O>[CH3:20][N:19]([CH3:21])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][S:8][C:6]1[NH:5][C:4](=[O:9])[CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 667493MethylthiouracilHCID 178486212HCID 178486212, compound

Product 1

HCID 1357442584(1H)-Pyrimidinone, 2-(((2-(dimethylamino)phenyl)methyl)thio)-6-methyl-Yield 78.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

After dissolving 0.71 g (5 mmol) of 6-methyl-2-thiouracil [Ann. 236, 1 (1986)] and 1.03 g (5 mmol) of (2-chloromethylphenyl)-dimethylammonium chloride (J. Chem. Soc. 1954, 4127) in 10 ml of dimethylsulfoxide, the reaction mixture is stirred at room temperature for 1 hour and then poured into 60 ml of water. After adjusting the pH value of the mixture to 6-8 by adding aqueous 1 N sodium hydroxide solution the precipitate is filtered and the crude base (1.3 g) is recrystallized from benzene to give 1.08 g (78.4%) of the title compound, m.p.: 152°-154° C. (white crystals).

Workup

  1. filtrationis filtered
  2. customthe crude base (1.3 g) is recrystallized from benzene

Sources & evidence

ORD record
ord-79dd19dc8cf34b809e623b3337661f31
Source dataset
uspto-grants-1991_08
Patent number
US05037830

Reaction notes

Loading…