HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 3-(2-Amino-4-chloro-6-methyl-pyrimidin-5-ylethynyl)-phenol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Chloro-5-iodo-6-methylpyrimidin-2-amine | HCID 11644720 | — |
| Reactant | 5-ethynyl-1H-pyrrolo[2,3-b]pyridine | HCID 55287981 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Product | 3-(2-Amino-4-chloro-6-methyl-pyrimidin-5-ylethynyl)-phenol | HCID 58513344 | — |
Reaction Steps
The title compound is synthesized according to general procedure GP2 starting from 500 mg (1.9 mmol) 4-chloro-5-iodo-6-methyl-pyrimidin-2-ylamine (GP3) and 396 mg (2.8 mmol) 5-ethynyl-1H-pyrrolo[2,3-b]pyridine (A-20) using 35 mg (0.19 mmol) CuI, 130 mg (0.19 mmol) PdCl2(PPh3)2 and 2.6 mL (19 mmol) triethylamine in 6 mL dry DMF. The product precipitates from the reaction mixture, is filtered off and washed with DMF. Yield: 436 mg (75%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08916548B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-9bb0f0c4419945a8b86f1db19323bb3f |
| Source note | uspto-grants-2014_12 |