HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 3-methyl-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diazaspiro[3.5]nonane-1-carboxylic acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro- | HCID 5356682 | — |
| Reactant | 3-Methyl-1,6-diazaspiro[3,5]nonane-1-carboxylic acid 1-benzyl ester | HCID 58293324 | — |
| Solvent | Water | HCID 962 | — |
| Product | 3-methyl-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diazaspiro[3.5]nonane-1-carboxylic acid benzyl ester | HCID 58293288 | 95.2% |
Reaction Steps
An optically-active compound of 3-methyl-1,6-diazaspiro[3,5]nonane-1-carboxylic acid 1-benzyl ester (2.20 g) was mixed with 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.17 g), potassium carbonate (3.17 g) and water (12 ml), and the mixture was stirred for 4 hours with refluxing. The mixture was cooled to room temperature, and extracted with chloroform twice. The combined organic layer was washed with water, 10% aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=1/0 to 1/3, followed by chloroform/methanol=95/5) to give the titled compound (2.84 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08609647B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-0647112b04e541c489006af262987ac8 |
| Source note | uspto-grants-2013_12 |