HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyridin-2-amine → N-(6-(6-amino-4-(trifluoromethyl)pyridin-3-yl)-2-morpholinopyrimidin-4-yl)-4-phenylthiazol-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyridin-2-amine | HCID 57416499 | — |
| Reactant | N-(6-chloro-2-morpholinopyrimidin-4-yl)-4-phenylthiazol-2-amine | HCID 59507613 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Sodium Carbonate | HCID 10340 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-(6-(6-amino-4-(trifluoromethyl)pyridin-3-yl)-2-morpholinopyrimidin-4-yl)-4-phenylthiazol-2-amine | HCID 59507621 | — |
Reaction Steps
A solution of N-(6-chloro-2-morpholinopyrimidin-4-yl)-4-phenylthiazol-2-amine (15 mg, 0.040 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyridin-2-amine (23 mg, 0.080 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride (6.6 mg, 0.0080 mmol) in 0.5 mL of 1,4-dioxane and 0.05 mL of 2 M aq. sodium carbonate was heated in the microwave at 120° C. for 600 seconds. The crude product was purified by reverse phase prep HPLC to give N-(6-(6-amino-4-(trifluoromethyl)pyridin-3-yl)-2-morpholinopyrimidin-4-yl)-4-phenylthiazol-2-amine. LC/MS (m/z): 500 (MH+), Rt 2.46 minutes.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08217035B2 |
| Source dataset | uspto-grants-2012_07 |
| ORD ID | ord-9aca640de49a4df3816e36a096f8d937 |
| Source note | uspto-grants-2012_07 |