HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N-methylglycine tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyl bromoacetate | HCID 79177 | — |
| Reactant | 6-(4-chlorophenyl)-3-(2-{4-[(methylamino)methyl]phenyl}ethyl)thieno[3,2-d]pyrimidin-4(3H)-one dihydrochloride | HCID 67359698 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N-methylglycine tert-butyl ester | HCID 59239843 | 71.9% |
Reaction Steps
A mixture of the compound (200 mg) obtained in Example 4, tert-butyl bromoacetate (89 mg), triethylamine (146 mg) and N,N-dimethylformamide (3 ml) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography [developing solvent:ethyl acetate-hexane (3:1, volume ratio)], and recrystallized from ethyl acetate-hexane (3:1, volume ratio) to give the title compound (156 mg) as a colorless powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07989445B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-00cc930835ce454b90cd8f93ec564d0c |
| Source note | uspto-grants-2011_08 |