Potassium Carbonate → HCID 14677248, compound

HRID 1534662Notes

Reaction equation

HRID 1534662 reaction equation
[NH2:1][N:2]1[C:6]([S:7][CH3:8])=[N:5][NH:4][C:3]1=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20](S(C)(=O)=O)[N:19]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.CC(C)=O>[NH2:1][N:2]1[C:6]([S:7][CH3:8])=[N:5][N:4]([C:20]2[N:21]=[C:22]([O:24][CH3:25])[CH:23]=[C:18]([O:17][CH3:16])[N:19]=2)[C:3]1=[O:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 14800563HCID 14800563, compound

Product 1

HCID 14677248HCID 14677248, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3.0 g (0.02 mol) of 4-amino-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one and 200 ml of acetone is refluxed for 4 hours after 0.1 g of p-toluenesulphonic acid has been added. The mixture is concentrated, the residue is taken up in 100 ml of acetonitrile, and the reaction mixture is refluxed for 12 hours after 8.3 g (0.06 mol) of potassium carbonate and 4.4 g (0.02 mol) of 4,6-dimethoxy-2-methylsulphonyl-pyrimidine have been added. The cooled mixture is filtered, the filtrate is concentrated, the residue is taken up in 100 ml of ethanol/water (vol. 1:1) and stirred for 3 hours at 60° C. after 2 ml of concentrated hydrochloric acid have been added. The mixture is concentrated, the residue is stirred with saturated sodium hydrogen carbonate solution, and the crystalline product is isolated by filtering off with suction. 4.9 g (86% of theory) of 4-amino-5-methylthio-2 -(4,6-dimethoxy-pyrimidin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 198° C. are obtained.

Workup

  1. additionhas been added
  2. concentrationThe mixture is concentrated
  3. additionhave been added
  4. filtrationThe cooled mixture is filtered
  5. concentrationthe filtrate is concentrated
  6. additionhave been added
  7. concentrationThe mixture is concentrated
  8. stirringthe residue is stirred with saturated sodium hydrogen carbonate solution
  9. customthe crystalline product is isolated
  10. filtrationby filtering off with suction

Sources & evidence

ORD record
ord-7f4b480796fe42e89533912841431d49
Source dataset
uspto-grants-1992_02
Patent number
US05089627

Reaction notes

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