Diisopropylethylamine → 8-METHOXY-[1,2,4]TRIAZOLO[1,5-A]PYRIDIN-2-AMINE

HRID 1057518Notes

Reaction equation

Cl.NO.C([N:6](C(C)C)C(C)C)C.[CH3:13][O:14][C:15]1[C:16]([NH:21][C:22]([NH:24]C(OCC)=O)=S)=[N:17][CH:18]=[CH:19][CH:20]=1>C(O)C.CO>[CH3:13][O:14][C:15]1[C:16]2[N:17]([N:6]=[C:22]([NH2:24])[N:21]=2)[CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 21.8 g (313.7 mmol) hydroxylamine hydrochloride and 32.2 ml (188.2 mmol) N-ethyldiisopropylamine in a mixture of 130 ml methanol ethanol 1:1 was added 16 g (62.7 mmol) N-(3-methoxy-2-pyridinyl)-N′-carboethoxy-thiourea and stirred for 2 h at room temperature and subsequently for 3 h at 60° C. The volatiles were removed under reduced pressure and the residue was triturated with 100 ml water. The collected precipitate was washed with 25 ml methanol/diethyl ether 4:1 and afterwards with 25 ml diethyl ether. After drying under high vacuum 8 g (78%, 48.7 mmol) of the title compound was collected as off-white crystals.

Workup

customThe volatiles were removed under reduced pressure
customthe residue was triturated with 100 ml water
washThe collected precipitate was washed with 25 ml methanol/diethyl ether 4:1 and afterwards with 25 ml diethyl ether

Sources & evidence

ORD record: ord-7560b44d7a344d9793a75e41a994d235
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06514989B1

Reaction notes

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