HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dimethoxyethane → 3-(2-Methoxy-5-trifluoromethyl-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Methoxy-5-(trifluoromethyl)phenylboronic acid | HCID 2782676 | — |
| Reactant | 3-Bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine | HCID 68962692 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Sulfuric acid magnesium salt (1:1) | HCID 24083 | — |
| Product | 3-(2-Methoxy-5-trifluoromethyl-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine | HCID 68962169 | — |
Reaction Steps
3-Bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (Intermediate 3) (0.1 g, 0.44 mmol), 2-methoxy-5-trifluoromethylphenylboronic acid (0.116 g, 0.53 mmol), Pd(dppf)Cl2 (0.032 g, 0.044 mmol), DME (4 ml) and 2M aqueous Na2CO3, are mixed together and heated using microwave radiation at 100° C. for 30 minutes. The reaction mixture is diluted with EtOAc (30 mls), MgSO4 is added and the resulting mixture is filtered through Celite® (filter agent), washing with EtOAc. The reaction mixture is absorbed onto silica and purification by flash chromatography on silica eluting with DCM then MeOH:DCM (5:95) affords the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08901134B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-00168a93f4b34f7ea02cf3664a97d02f |
| Source note | uspto-grants-2014_12 |