Hydrochloric Acid → 2-Isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine

HRID 1802197Notes

Reaction equation

[CH:1]([C:4]1[N:20]=[C:7]2[CH:8]=[C:9]([NH:12]C(=O)OC(C)(C)C)[CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].Cl>O1CCCC1>[CH:1]([C:4]1[N:20]=[C:7]2[CH:8]=[C:9]([NH2:12])[CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of tert-butyl 2-isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (400 mg, 1.45 mmol) in tetrahydrofurane (10 ml) is added hydrochloric acid (5 N in diethyl ether, 20 ml, 100 mmol). The resulting suspension is stirred for 18 hours at 25° C. The solvent is evaporated and the residue diluted with ethyl acetate, made basic with sodium hydroxide 2N and washed with water and brine. The organic layer is dried with magnesium sulfate and the solvent is evaporated under reduced pressure. The residue (416 mg) is purified by chromatography on a 20 g silicagel column using heptane/ethyl acetate 50-100% as eluent affording 2-isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine (159 mg, 62.3%) as a white solid. Mp.: 174-6° C. MS: m/z=177.2 (M+H+).

Workup

customThe solvent is evaporated
additionthe residue diluted with ethyl acetate
washwashed with water and brine
dry with materialThe organic layer is dried with magnesium sulfate
customthe solvent is evaporated under reduced pressure
customThe residue (416 mg) is purified by chromatography on a 20 g silicagel column

Sources & evidence

ORD record: ord-7e5799e48443403bb646a05038fb75ac
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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