HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → 3-[(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine | HCID 46180726 | — |
| Reactant | tert-Butyl 3-methanesulfonamidopyrrolidine-1-carboxylate | HCID 67189774 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-[(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 86618407 | 48.4% |
Reaction Steps
To a solution of 3-Methanesulfonylamino-pyrrolidine-1-carboxylic acid tert-butyl ester (0.47 g) in DMF (5 mL) was added NaH (63 mg). The mixture was stirred for 40 min. then a solution of 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (0.52 g) in DMF (5 mL) was added via cannular. The resulting mixture was stirred at R.T. for 5 h. An aqueous work-up followed by purification on silica gave 3-[(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester (384 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08450315B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-c522cd548e724f678fd1febf17c71610 |
| Source note | uspto-grants-2013_05 |