Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | HCID 68325557 | HCID 68325557 | — |
| Solvent | Tetrahydrofuran ethyl acetate | HCID 21939870 | — |
| Product | HCID 68325483 | HCID 68325483 | 70.1% |
Reaction Steps
(R)-tert-Butyl 2-(4-(5-(difluoromethoxy)pyrimidin-2-ylamino)phenyl)morpholine-4-carboxylate (58 mg) was combined with acetonitrile (2 ml) and water (6 ml). Trifluoroacetic acid (138 μl) was added. The vial was capped and shaken at 80° C. for 4 hours. The reaction mixture was then poured into EtOAc/THF (1:1) and washed with 1 M aq. NaOH. The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/EtOAc/MeOH) to afford (R)-5-(difluoromethoxy)-N-(4-(morpholin-2-yl)phenyl)pyrimidin-2-amine (31 mg, 70%) as a white solid. MS (ISP): 323.1 ([M+H]+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08802673B2 |
|---|
| Source dataset | uspto-grants-2014_08 |
|---|
| ORD ID | ord-aaeb6efb572944398889be9327598901 |
|---|
| Source note | uspto-grants-2014_08 |
|---|