Triethylamine → HCID 19045207, compound

HRID 1085287Notes

Reaction equation

HRID 1085287 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 were dissolved in 280 ml of pyridine, followed by the addition of 45.5 g of triethylamine and 21.3 g of aminoethanol. The thus-prepared mixture was heated under reflux at 90° C. for 4 hours. The reaction mixture was ice-cooled and while maintaining the internal temperature at 0°-4° C., 55.8 g of methanesulfonyl chloride were added dropwise. The resultant mixture was stirred for 3 hours at the same temperature. 1.2 l of methanol were added, followed by stirring for additional 2 hours. Crytals precipitated in the reaction mixture were collected by filtration and then recrystallized from 3.5 l of methanol, thereby obtaining 70.0 g of 1,3-dimethyl-6-(2-methanesulfonyloxyethylamino)-2,4(1H,3H)-pyrimidinedione (Compound c) as crystals.

Workup

  1. temperatureThe thus-prepared mixture was heated
  2. temperaturecooled
  3. temperaturewhile maintaining the internal temperature at 0°-4° C.
  4. customCrytals precipitated in the reaction mixture
  5. filtrationwere collected by filtration
  6. customrecrystallized from 3.5 l of methanol

Sources & evidence

ORD record
ord-627684e4b58d4e3688e0f2db83f84dc2
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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