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

HRID 1972976Notes

Reaction equation

[NH2:1][N:2]1[CH:6]=[C:5]([C:7]#[N:8])[CH:4]=[C:3]1[C:9]#[N:10].C(O)(=O)C.[CH:15](N)=[NH:16].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CCO>[NH2:10][C:9]1[C:3]2=[CH:4][C:5]([C:7]#[N:8])=[CH:6][N:2]2[N:1]=[CH:15][N:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-Amino-1H-pyrrole-2,4-dicarbonitrile (3.00 g, 22.71 mmol), formamidine acetate (22.71 g, 272.47 mmol) and K2CO3 (43.93 g, 317.88 mmol) were diluted in EtOH (105 mL). The mixture was heated at 80° C. for 2 h and then cooled to rt. EtOAc (200 mL) was added and the organic layer was washed with water (100 mL), dried over MgSO4 and then concentrated to dryness. The crude material was purified by ISCO® chromatography to afford the desired product (2.58 g, 71%). 1H NMR (400 MHz, DMF-d6) δ 7.91 (s, 1H), 7.64 (s, 1H), 7.61 (s, 1H), 7.21 (s, 2H); LC-MS m/z[M+H]+ 159.9, RT 1.21 min.

Workup

temperaturecooled to rt
washthe organic layer was washed with water (100 mL)
dry with materialdried over MgSO4
concentrationconcentrated to dryness
customThe crude material was purified by ISCO® chromatography

Sources & evidence

ORD record: ord-a10d6009971a42ccbe0119f749c651e5
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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