HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (S)2-[(5-Bromo-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-carboxylic acid tert butyl carbonate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-Bromo-2-chloropyrimidine | HCID 606665 | — |
| Reactant | tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylate | HCID 1512533 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | (S)2-[(5-Bromo-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-carboxylic acid tert butyl carbonate | HCID 86593681 | 85% |
Reaction Steps
(S)-2-Aminomethyl-pyrrolidine-1-carboxylic acid tert butyl ester (2 g), 5-bromo-2-chloropyrimidine (1.93 g) were combined in xylene (40 ml) containing potassium carbonate (2.76 g) and diisopropylethylamine (5.23 ml) and warmed to reflux for 20 h. The mixture was cooled to room temperature, filtered and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, pentane-25% ethyl acetate/pentane). The appropriate fractions were collected, solvent removed at reduced pressure to give the title compound (1.78 g) as a colourless gum
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07741329B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-2bdfc3f175964d7eb5c13d543d883d16 |
| Source note | uspto-grants-2010_06 |