Triethylamine → HCID 19045207, compound

HRID 1032970Notes

Reaction equation

HRID 1032970 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[CH:3]=1.[CH2:12]([N:14](CC)CC)[CH3:13].NC([OH:22])C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1.CO>[CH3:8][N:7]1[C:2]([NH:14][CH2:12][CH2:13][O:25][S:24]([CH3:23])(=[O:26])=[O:22])=[CH:3][C:4](=[O:11])[N:5]([CH3:10])[C:6]1=[O:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 814426-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedioneHCID 522583Acetaldehyde ammonia

Product 1

HCID 19045207HCID 19045207, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

52.4 g of 6-chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione was dissolved in 280 ml of pyridine, and 45.5 g of triethylamine and 21.3 g of aminoethanol were further added thereto. Afterward, the solution was heated with stirring at 90° C. for 4 hours. The reaction solution was ice-cooled so as to maintain its internal temperature at a level of from 0° to 4° C., and 55.8 g of methanesulfonyl chloride was added dropwise thereto. The solution was then stirred at the same temperature for 3 hours, and 1.2 liters of methanol was added thereto, followed by stirring for 2 hours. Crystals precipitated in this reaction solution were collected by filtration and further recrystallized from 3.5 liters of methanol to obtain 70.0 g of crystalline 1,3-dimethyl-6-(2-methanesulfonyloxyethylamino)-2,4-(1H,3H)-pyrimidinedione (Compound a).

Workup

  1. temperatureAfterward, the solution was heated
  2. temperaturecooled so as
  3. additionwas added dropwise
  4. stirringThe solution was then stirred at the same temperature for 3 hours
  5. stirringby stirring for 2 hours
  6. customCrystals precipitated in this reaction solution
  7. filtrationwere collected by filtration
  8. customfurther recrystallized from 3.5 liters of methanol

Sources & evidence

ORD record
ord-054bf538a6454274a17afe6777872347
Source dataset
uspto-grants-1994_05
Patent number
US05308848

Reaction notes

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