HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → tert-butyl 4-[6-(2,5-dimethoxyphenyl)-1-[(2-ethyl-2H-tetrazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2,5-Dimethoxyphenylboronic acid | HCID 2734342 | — |
| Reactant | Tert-butyl 4-[6-bromo-1-[(2-ethyl-2H-tetrazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate | HCID 67258602 | — |
| Catalyst | Dichlorobis(tricyclohexylphosphine)pallium (II) | HCID 11050900 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | tert-butyl 4-[6-(2,5-dimethoxyphenyl)-1-[(2-ethyl-2H-tetrazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate | HCID 67259968 | — |
Reaction Steps
Tert-butyl 4-[6-bromo-1-[(2-ethyl-2H-tetrazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate (203 mg, compound B101), (2,5-dimethoxyphenyl)boronic acid (100 mg), dichlorobis(tricyclohexylphosphine)palladium (37 mg) and aqueous cesium carbonate solution (0.375 ml, 2.0 M) in DME (10 ml) are reacted according to the procedure described in example B55 to afford the title compound after purification by flash column chromatography [silica gel, elution gradient: cyclohexane/EtOAc, 100/0 to 50/50 to 30/70 (v/v)] as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09018175B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-43100c45c10848a3acd44eee25ff749e |
| Source note | uspto-grants-2015_04 |