Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Furan-2-boronic acid | HCID 2734357 | — |
| Reactant | 2,5-dichloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine | HCID 59586799 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 50942862 | HCID 50942862 | 9% |
Reaction Steps
The mixture of Pd(dppf)Cl2.CH2Cl2 (100 mg, 0.12 mmol, 0.15 eq), furan-2-ylboronic acid (116 mg, 1.04 mmol, 1.3 eq), 2,5-dichloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (215 mg, 0.80 mmol, 1.0 eq) and aq Na2CO3 (10 mL) in dioxane (20 mL) was heated to 95° C. for 2 h under nitrogen atmosphere. The reaction mixture was cooled to room temperature, and extracted with THF. The combined layers were purified by prep-HPLC to afford compound 5-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-(furan-2-yl)pyrimidin-4-amine (Compound 164) (12 mg, 9%). LC-MS (m/z)=302 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 0.73-0.76 (m, 2H), 0.95-0.98 (m, 2H), 1.93-1.97 (m, 1H), 6.53 (s, 1H), 6.68-6.70 (m, 1H), 7.15 (d, J=2.8 Hz, 1H), 7.91 (s, 1H), 8.41 (s, 1H), 9.24 (s, 1H), 12.24 (s, 1 Hz).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09422271B2 |
|---|
| Source dataset | uspto-grants-2016_08 |
|---|
| ORD ID | ord-afc3a19e4c644da6b0a41c141844c6ca |
|---|
| Source note | uspto-grants-2016_08 |
|---|
