Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Tributylvinyltin | HCID 81998 | — |
| Reactant | 1,1-Dimethylethyl (1S,4S)-5-(5-bromo-2-pyrimidinyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate | HCID 58190411 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66940125 | HCID 66940125 | 35.7% |
Reaction Steps
(S,S)-5-(5-Bromo-pyrimidin-2-yl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (177 mg, 0.5 mmol), tributyl vinyl tin (634 mg, 2 mmol) and Cl2Pd(dppf)CH2Cl2 (60 mg) was mixed in DMF (3 mL). The mixture was heated at 90° C. over 3 days. The cooled down reaction was participate between ethyl acetate (50 mL) and H2O (10 mL). The organic layer was washed with H2O (10 mL), brine (10 mL), dried (MgSO4) and filtered. The conc. filtrate was purified on silica gel column eluting with 33% to 50% ethyl acetate/hexanes to yield the title compound as a white solid (54 mg). MS (303, MH).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08546404B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-0b363c07576d4cf9b6ea41511d91155f |
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| Source note | uspto-grants-2013_10 |
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