Ethanol → 4-Aminopyrrolo[2,1-F][1,2,4]triazine-6-carbonitrile

HRID 73666Notes

Reaction equation

CCO.[NH2:4][N:5]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[C:6]1[C:12]#[N:13].C(O)(=O)C.[CH:18](N)=[NH:19].C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O>[NH2:13][C:12]1[C:6]2=[CH:7][C:8]([C:10]#[N:11])=[CH:9][N:5]2[N:4]=[CH:18][N:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of EtOH (50 mL) was added 1-amino-1H-pyrrole-2,4-dicarbonitrile (1.00 g, 7.57 mmol) followed by formamidine acetate (9.46 g, 90.8 mmol) and potassium carbonate (14.6 g, 106.0 mmol). The solution was heated to 80° C. for 2 h. Upon cooling to rt, the reaction mixture was diluted with EtOAc transferred to a separatory funnel and washed with water. The organic layer was collected, dried (MgSO4), filtered, and concentrated to dryness. The crude material was then triturated with EtOH-water. The solid was collected, washed with water, and dried under vacuum to afford 0.91 g of the above compound as a yellow-orange solid (5.70 mmol, yield 75%). 1H-NMR (DMSO-d6) δ 8.37 (d, J=1.8 Hz, 1H), 8.19 (d, J=17.4, 2H), 7.93 (s, 1H), 7.27 (d, J=1.8 Hz, 1H); LCMS RT=1.14 min.

Workup

temperatureUpon cooling to rt
customtransferred to a separatory funnel
washwashed with water
customThe organic layer was collected
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated to dryness
customThe crude material was then triturated with EtOH-water
customThe solid was collected
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-3bbf0b6a0bcf4214a110a8f25a72a24e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829185B2

Reaction notes

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