HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro- | HCID 5356682 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine | HCID 265829 | 88% |
Reaction Steps
According to Scheme 5, cesium carbonate (968 mg, 3 mmol) followed by methyl iodide (1 g, 7.1 mmol) was added to a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (121 mg, 0.79 mmol) in DMF (5 mL). The mixture was stirred at room temperature for 6 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried, concentrated and column chromatographed to give 116 mg (88%) of 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine as a white solid. 1H NMR (360 MHz, DMSO-d6) 8.62 (s, 1H), 7.71 (s, 1H), 6.62 (s, 1H), 3.84 (s, 3H, CH3).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06610688B2 |
| Source dataset | uspto-grants-2003_08 |
| ORD ID | ord-a110dd028d084fa8af55e563f9c61804 |
| Source note | uspto-grants-2003_08 |