Formamidine acetate → 3-(1H-benzimidazol-2-ylmethyl)-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one
Reaction equation
[NH2:1][C:2]1[C:3](=[O:20])[NH:4][C:5](=[S:19])[N:6]([CH2:9][C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]=2)[C:7]=1[NH2:8].[C:21](O)(=O)C.C(N)=N>CS(C)=O>[NH:11]1[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=[C:10]1[CH2:9][N:6]1[C:7]2[N:8]=[CH:21][NH:1][C:2]=2[C:3](=[O:20])[NH:4][C:5]1=[S:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 5,6-diamino-1-(1H-benzimidazol-2-ylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (0.19 g, 0.65 mmol, obtained from Example 8(c)) in DMSO (2 mL) was added formamidine acetate (0.10 g, 0.98 mmol). The reaction mixture was heated to 70° C. for 2 h. Purification of the crude product using preparative HPLC gave the title compound (0.029 g, 15%) as a solid.
Workup
- customPurification of the crude product
Sources & evidence
- ORD record
- ord-24be4427dd2f4892bb13ad4abf64cea7
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026244B2
Reaction notes
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