Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | HCID 89422280 | HCID 89422280 | — |
| Reactant | 2-(2-Aminopyridin-4-yl)-4-chlorophenol | HCID 136063619 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | HCID 71283739 | HCID 71283739 | 88.3% |
Reaction Steps
A mixture of 2-(2-aminopyridin-4-yl)-4-chlorophenol (110 mg, 0.5 mmol), (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-chloropyrimidine-4-carboxamide (122 mg, 0.5 mmol), CuI (10 mg, 0.05 mmol) and Cs2CO3 (191 mg, 0.5 mmol) in DMF (3 mL) was stirred at 120° C. for 4 hrs. The reaction mixture was cooled to room temperature, worked up with dichloromethane and subjected to flash chromatography (DCM/methanol) to give (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(2-(2-aminopyridin-4-yl)-4-chlorophenoxy)pyrimidine-4-carboxamide as a white solid (189 mg, yield 85%). 1H NMR (CD3OD): 7.82-8.05 (1H, br), 7.6 (2H, m), 7.40 (2H, m), 6.80 (1H, m), 6.60 (2H, m), 4.23-4.10 (1H, m), 1.35 (3′-1, d, J=7.0 Hz). LC/MS: m/z=428 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09163008B2 |
|---|
| Source dataset | uspto-grants-2015_10 |
|---|
| ORD ID | ord-a2c8d90af7f1460c91dd475fa96c0cc7 |
|---|
| Source note | uspto-grants-2015_10 |
|---|
