Formamide → thieno(2,3-d)pyrimidin-4(3H)-one
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9]C)=O.[CH:11]([NH2:13])=O>O>[N:1]1[C:2]2[S:3][CH:4]=[CH:5][C:6]=2[C:7](=[O:9])[NH:13][CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 190 °C
Procedure
Methyl 2-aminothiophene-3-carboxylate (10 g, 64 mmol) was charged with formamide (50 mL). The reaction was heated at 190° C. under nitrogen for 3 hours, then cooled to ambient temperature. The resulting slurry was poured into 125 mL of water and extracted with chloroform:isopropyl alcohol mixture (2 times). The solution was concentrated and triturated to afford the title compound (2.25 g, 23%).
Workup
- temperaturecooled to ambient temperature
- extractionextracted with chloroform
- concentrationThe solution was concentrated
- customtriturated
Sources & evidence
- ORD record
- ord-7788c127afbb4fab9df763a564d3fbfb
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362037B2
Reaction notes
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