HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine → 6-(3-aminopyridin-4-yl)-N,N-di-BOC-2-(methylthio)pyrimidin-4-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 | HCID 86669199 | HCID 86669199 | — |
| Catalyst | HCID 178418807 | HCID 178418807 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 6-(3-aminopyridin-4-yl)-N,N-di-BOC-2-(methylthio)pyrimidin-4-amine | HCID 69044381 | 32% |
Reaction Steps
Method 26 was followed using 6-chloro-N,N-di-BOC-2-(methyl-thio)pyrimidin-4-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 6-(3-aminopyridin-4-yl)-N,N-di-BOC-2-(methyl-thio)pyrimidin-4-amine in 32% yield. LCMS (m/z): 434.2 (MH+); LC Rt=3.56 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822497B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-370a64d3a18d470188e1a0013fe53baa |
| Source note | uspto-grants-2014_09 |