Triethylamine → HCID 19045207, compound

HRID 1729282Notes

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

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 added thereto, followed by stirring at 90° C. for 4 hours. The reaction solution was cooled with ice so that its internal temperature might be in the range of from 0° to 4° C., and 55.8 g of methanesulfonyl chloride was added dropwise thereto, and the solution was then stirred at the same temperature for 3 hours. 1.2 liters of methanol were added to the solution, followed by stirring for further 2 hours. The crystals which had been deposited in the reaction solution were collected by filtration and then 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 m), which had a melting point of from 169° to 170° C.

Workup

temperatureThe reaction solution was cooled with ice so that its internal temperature
additionwas added dropwise
stirringthe solution was then stirred at the same temperature for 3 hours
stirringby stirring for further 2 hours
filtrationwere collected by filtration
customrecrystallized from 3.5 liters of methanol

Sources & evidence

ORD record: ord-0faf70ba14ae4a09bc6191f8a5508b95
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05332739

Reaction notes

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