HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dimethoxyethane → (R)-5',5'-Difluoro-6-(pyrimidin-5-yl)-2,3,5',6'-tetrahydrospiro[indene-1,4'-[1,3]oxazin]-2'-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | (Pyrimidin-5-yl)boronic acid | HCID 2795193 | — |
| Reactant | (R)-6-bromo-5',5'-difluoro-2,3,5',6'-tetrahydrospiro[indene-1,4'-[1,3]oxazin]-2'-amine | HCID 71059702 | — |
| Solvent | Water | HCID 962 | — |
| Product | (R)-5',5'-Difluoro-6-(pyrimidin-5-yl)-2,3,5',6'-tetrahydrospiro[indene-1,4'-[1,3]oxazin]-2'-amine | HCID 71059374 | 19% |
Reaction Steps
In a manner analogous to that described in Example 1, the cross-coupling reaction of (R)-6-bromo-5′,5′-difluoro-2,3,5′,6′-tetrahydrospiro[indene-1,4′-[1,3]oxazin]-2′-amine (intermediate A6.5) with pyrimidin-5-ylboronic acid in a 3:1-mixture of 1,2-dimethoxyethane and water as the solvent yielded the title compound (19% yield) as an off-white solid. MS (ISP): m/z=317.0 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09079919B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-ddcd8176b4fd460f8654470a429c7b7a |
| Source note | uspto-grants-2015_07 |