Diisopropylethylamine → 5-Bromo-7-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 1472869Notes

Reaction equation

Cl.NO.C([N:7](C(C)C)CC)(C)C.[Br:13][C:14]1[N:19]=[C:18]([NH:20][C:21]([NH:23]C(OCC)=O)=S)[CH:17]=[C:16]([CH3:29])[CH:15]=1>C(O)C.CO>[Br:13][C:14]1[N:19]2[N:7]=[C:21]([NH2:23])[N:20]=[C:18]2[CH:17]=[C:16]([CH3:29])[CH:15]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of hydroxylamine hydrochloride (0.65 g, 9.27 mmol) in ethanol/methanol (1:1, 20 ml) was added diisopropylethylamine (0.97 ml, 5.56 mmol) and the mixture was stirred at room temp. (20° C.) for 1 h. 1-(6-Bromo-4-methyl-pyridin-2-yl)-3-carboethoxy-thiourea (0.59 g, 1.84 mmol) was added and the mixture slowly heated to reflux. Having refluxed overnight the mixture was allowed to cool and filtered to collect the precipitated solid. Further product was collected by evaporation in vacuo of the filtrate, addition of water and filtration. The combined solids were washed successively with water, ethanol/methanol and diethylether, then dried in vacuo to give the desired product. Yield 0.19 g, 45%. LCMS MI: 226.91+228.89, RT: 2.52 min, Method: 2

Workup

temperaturethe mixture slowly heated to reflux
temperatureHaving refluxed overnight the mixture
temperatureto cool
filtrationfiltered
customto collect the precipitated solid
filtrationFurther product was collected by evaporation in vacuo of the filtrate, addition of water and filtration
washThe combined solids were washed successively with water, ethanol/methanol and diethylether
customdried in vacuo

Sources & evidence

ORD record: ord-412f11ab4e8e4d669b0a301fbd2027f4
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012633B2

Reaction notes

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