1-Butanol → 2-Methylpyrrolo(2,1-f)(1,2,4)triazin-4-amine
Reaction equation
Cl.N[N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]#[N:9].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl.[C:19]([NH2:22])(=[NH:21])[CH3:20].C(O)CCC>>[CH3:20][C:19]1[N:22]=[C:8]([NH2:9])[C:4]2=[CH:5][CH:6]=[CH:7][N:3]2[N:21]=1Participants
Procedure
A mixture of 1-amino-1H-pyrrole-2-carbonitrile hydrochloride (2.77 g, 19.3 mmol), potassium phosphate (21.11 g, 96.5 mmol), acetamidine hydrochloride (9.6 g, 96.5 mmol) and 1-butanol (166 mmol) was refluxed under nitrogen atmosphere. After 166.5 h of reflux, the mixture was allowed to cool to rt, and was then partitioned between ethyl acetate and water. The phases were separated, and the organic phase was extracted with 1N aqueous hydrochloric acid. The acid extracts were made basic (pH>7) and extracted with ethyl acetate. After washing the organic layers with water and brine, drying (anhydrous sodium sulfate) and concentration afforded 1.63 g (57%) of solid. 1H-NMR (CD2Cl2): δ 7.51 (m, 1 H), 6.40 (m, 2 H), 6.72 (br s, 2 H), 2.32 (s, 3 H). MS: LC/MS (+esi), m/z=149 [M+H]. RT=1.12 min.
Workup
- temperaturewas refluxed under nitrogen atmosphere
- temperatureAfter 166.5 h of reflux
- customwas then partitioned between ethyl acetate and water
- customThe phases were separated
- extractionthe organic phase was extracted with 1N aqueous hydrochloric acid
- extractionextracted with ethyl acetate
- washAfter washing the organic layers with water and brine
- customdrying
- concentration(anhydrous sodium sulfate) and concentration
Sources & evidence
- ORD record
- ord-9f1b089520aa488b91a2c31068fcaede
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431695B2
Reaction notes
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