Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | HCID 58073044 | HCID 58073044 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Product | HCID 58072584 | HCID 58072584 | — |
Reaction Steps
The title compound is synthesized according to general procedure GP4 starting from 2.5 g (9.7 mmol) 4-chloro-6-ethyl-5-(6-amino-pyridin-3-ylethynyl)-pyrimidine using 2.4 g (11.6 mmol) 3-methoxy-4-methoxycarbonylphenyl boronic acid, 339 mg (0.48 mmol) bis-(triphenylphoshine)palladium(II) chloride, 14 mL (28.2 mmol) of an aqueous 2 M Cs2CO3 and 5 mL MeOH in 50 mL DME. The reaction mixture is stirred for 2 hours at 90° C. The solvent is removed under reduced pressure and the residue is taken up in water and ethylacetate. The aqueous phase is extracted twice with ethylacetate. The combined organic layers are dried over MgSO4 filtered over celite and the solvent is removed under reduced pressure. After drying 3.3 g (89%) of the desired product is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09321771B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-ad239c9588594d1296e850b48d53cebb |
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| Source note | uspto-grants-2016_04 |
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