HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Aminopyrimidine → 3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-pyrimidin-4-yl-propionamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Aminopyrimidine | HCID 68958 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | (S)-3-Cyclohexyl-2-(1-oxoisoindolin-2-yl)propanoic acid | HCID 1477119 | — |
| Reactant | (R)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide | HCID 10133709 | — |
| Product | 3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-pyrimidin-4-yl-propionamide | HCID 18402221 | 74.4% |
Reaction Steps
BOP coupling of (S)-3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Example 1, Step A; 287 mg; 1.00 mmol) and 4-aminopyrimidine (108 mg; 1.14 mmol) in a manner similar to that used for the preparation of (R)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide (outlined in Example 9, Step B) provided after flash chromatography (Merck Silica gel 60, 230-400 mesh, eluent: 50% ethyl acetate/hexanes) 271 mg (74%)of 3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-pyrimidin-4-yl-propionamide as a white foam: EI-HRMS m/e calcd for C21H24N4O2 (M+) 364.1899, found 364.1893.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06482951B2 |
| Source dataset | uspto-grants-2002_11 |
| ORD ID | ord-4d816b43d9d9430aaa21891b4e41ac64 |
| Source note | uspto-grants-2002_11 |