Butanoic acid, 2,3-dibromo-, ethyl ester → 2-benzylsulfanyl-7-methyl-1H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one

HRID 844959Notes

Reaction equation

Br[CH:2]([CH:8](Br)[CH3:9])[C:3]([O:5]CC)=O.[NH2:11][C:12]1[N:16]=[C:15]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:14][N:13]=1>N1C=CC=CC=1>[CH2:18]([S:17][C:15]1[N:16]=[C:12]2[N:11]=[C:3]([OH:5])[CH:2]=[C:8]([CH3:9])[N:13]2[N:14]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Ethyl 2,3-dibromobutyrate (1.33 g, 48.5 mmol) was added dropwise over 15 minutes to a solution of 10 g (49 mmol) of 3-amino-5 -benzylthio-1,2,4-triazole in 20 ml of pyridine heated to 65° C. After the addition was complete, the reaction mixture was heated at 65° C. for 20 hours, cooled to room temperature and filtered. The filtrate was concentrated by evaporation at reduced pressure. The residue was triturated with methanol to separate 1.64 g (13%) of the desired product as a colorless crystalline solid, m.p. 219°-220° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

additionAfter the addition
temperaturethe reaction mixture was heated at 65° C. for 20 hours
temperaturecooled to room temperature
filtrationfiltered
concentrationThe filtrate was concentrated by evaporation at reduced pressure
customThe residue was triturated with methanol
customto separate 1.64 g (13%) of the desired product as a colorless crystalline solid, m.p. 219°-220° C

Sources & evidence

ORD record: ord-9eca868858794a19913d5cf0c5d5ccce
Source dataset: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04755212

Reaction notes

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