Carbon Disulfide → HCID 820638, compound

HRID 2036277Notes

Reaction equation

HRID 2036277 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[CH:3]=1.[OH-].[Na+].[C:14](=[S:16])=[S:15].S(OC)(O[CH3:21])(=O)=O>CS(C)=O.O>[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[C:3]=1[C:14]([S:16][CH3:21])=[S:15]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 811526-Amino-1,3-dimethyluracil

Product 1

HCID 820638HCID 820638, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 6-amino-1,3-dimethyl uracil (50.0 g, 322.24 mmol) in DMSO (488 ml) was added dropwise a solution of 8 N sodium hydroxide (96.6 ml) and carbon disulphide (12.53 ml, 209.45 mmol) at 0° C. The resulting reaction mixture was vigorously stirred at room temperature for 30 min. The reaction mixture was cooled to 0-5° C. and dimethyl sulphate (31 ml, 418 mmol) was added dropwise over a period of 30 min. The reaction mixture was then slowly warmed to room temperature and stirred further for 3 h. The mixture was then diluted with water (500 ml) and precipitated solid was collected by filtration to give 30.2 g of the product as a yellow solid; 1H NMR (300 MHz, CF3COOD) δ 2.73 (s, 3H), 3.51 (s, 3H), 3.62 (s, 3H).

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe reaction mixture was cooled to 0-5° C.
  3. temperatureThe reaction mixture was then slowly warmed to room temperature
  4. stirringstirred further for 3 h
  5. customprecipitated solid
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-c2d57490314b4d89b19d32ba2d9f026f
Source dataset
uspto-grants-2013_11
Patent number
US08575178B2

Reaction notes

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