Formamidine acetate → 3-[2-(1H-Benzimidazol-2-yl)ethyl]-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one
Reaction equation
[NH2:1][C:2]1[C:3](=[O:21])[NH:4][C:5](=[S:20])[N:6]([CH2:9][CH2:10][C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[N:12]=2)[C:7]=1[NH2:8].[C:22](O)(=O)C.C(N)=N>CS(C)=O>[NH:12]1[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=[C:11]1[CH2:10][CH2:9][N:6]1[C:7]2[N:8]=[CH:22][NH:1][C:2]=2[C:3](=[O:21])[NH:4][C:5]1=[S:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To 5,6-diamino-1-[2-(1H-benzimidazol-2-yl)ethyl]-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (0.29 g, 0.96 mmol, obtained from Example 12(c)) in DMSO (2 mL) was added formamidine acetate (0.15 g, 1.4 mmol) and the reaction was heated to 80° C. for 2 h. Purification of the crude product using preparative HPLC gave the title compound (0.035 g, 12% yield).
Workup
- customPurification of the crude product
Sources & evidence
- ORD record
- ord-f98d2907b1e2408eae10166c1ee07bfa
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026244B2
Reaction notes
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