HuagongsheHuagongshe Chemistry Print Report · For research reference only
Formaldehyde → Ethyl 2-(4-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenyl)-3-hydroxypropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Ethyl 2-(4-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenyl)acetate | HCID 68727105 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Ethyl 2-(4-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenyl)-3-hydroxypropanoate | HCID 68729053 | — |
Reaction Steps
Ethyl 2-(4-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenyl)acetate 31 (1 mmol) and paraformaldehyde (5 mmol.) are dissolved in dry DMSO (0.2-0.5M) and heated at 70° C. in the presence of Na2CO3 (5 mmol.) for 2-6 h until greater than 50% conversion is achieved by LC/MS monitoring. The mixture is diluted with EtOAc and washed with water. After concentration, the residue is purified by silica gel chromatography to yield ethyl 2-(4-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenyl)-3-hydroxypropanoate 32. MS (m/z) (M+1)+: 432.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08293757B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-80604fa1c017485a9d936b69cc406f4c |
| Source note | uspto-grants-2012_10 |