HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine → 4-(3-aminopyridin-4-yl)-6-methoxy-N,N-di-BOC-pyrimidin-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine | HCID 49760414 | — |
| Reactant | 4-chloro-N,N-di-BOC-6-methoxypyrimidin-2-amine | HCID 86669198 | — |
| Catalyst | HCID 178418807 | HCID 178418807 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 4-(3-aminopyridin-4-yl)-6-methoxy-N,N-di-BOC-pyrimidin-2-amine | HCID 69044113 | 13% |
Reaction Steps
Method 26 was followed using 4-chloro-N,N-di-BOC-6-methoxypyrimidin-2-amine (1.0 equiv.), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-3-amine (3.0 equiv.), Pd(dppf)Cl2-DCM (0.10 equiv.) in DME/2M Na2CO3 (0.07M) at 90° C. for 30 min. Purification via SiO2 column chromatography eluting with EtOAc and hexanes (1:1) afforded 4-(3-aminopyridin-4-yl)-6-methoxy-N,N-di-BOC-pyrimidin-2-amine in 13% yield). LCMS (m/z): 418.1 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822497B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-0a94b936284f4a4d93ae2ab071441e34 |
| Source note | uspto-grants-2014_09 |