HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 6-[2,3-Dihydro-2-oxo-1H-benzimidazol-1-ylmethyl]-1,2,3,4-tetrahydro-3-methyl-1-(isobutyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-5-carboxylic acid, methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Chlorobenzimidazole | HCID 78572 | — |
| Reactant | 6-[(4,5-Dichloro-2-methyl-1H-imidazol-1-yl)methyl]-5-[4-(S)-hydroxy-2-isoxazolidinylcarbonyl]-3-methyl-1-(isobutyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione | HCID 10142559 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 6-[2,3-Dihydro-2-oxo-1H-benzimidazol-1-ylmethyl]-1,2,3,4-tetrahydro-3-methyl-1-(isobutyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-5-carboxylic acid, methyl ester | HCID 86622711 | — |
Reaction Steps
The product of example 3 part b) (0.5 g, 1.28 mmol), 2-chlorobenzimidazole (0.21 g, 1.37 mmol), potassium carbonate (0.36 g, 2.6 mmol) and DMF (10 ml) were stirred for 1.5 h. Ethyl acetate and water were added to the reaction mixture. The two phases were separated, the organic layer was dried (MgSO4) and then concentrated in vacuo. The residue was purified by biotage eluting with dichloromethane to give the sub-title compund as a pale yellow solid, 0.36 g (61%). δ 1HD6DMSO 0.83 and 0.91 (6H, d), 2.1-2.22 (1H,m), 3.38 (3H,s), 3.67 (2H,d), 4.1 (3H,s), 5.58 (2H,s), 7.26-7.38 (2H,m), 7.41-7.48 (1H,m) and 7.7-7.8 (1H,m).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07384950B2 |
| Source dataset | uspto-grants-2008_06 |
| ORD ID | ord-56eb70ac79244e5a9cba5c5fb95804f0 |
| Source note | uspto-grants-2008_06 |