Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Propanoic acid, 2-bromo-2-methyl-, ethyl ester | HCID 11745 | — |
| Reactant | HCID 57636039 | HCID 57636039 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69063981 | HCID 69063981 | 62% |
Reaction Steps
A mixture of 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenol (400 mg, 1.14 mmol, Example 35(p)], Cs2CO3 (1.1 g, 3.41 mmol), and ethyl 2-bromo-2-methylpropionate (0.5 mL, 3.41 mmol) in N,N′-dimethylformamide (4 mL) is heated to 60° C. for 15 hours. The reaction mixture is diluted with water, and extracted with ethyl acetate. The extracts are dried over magnesium sulfate, filtered and concentrated. The residue is subjected to chromatography on silica gel eluting with 50% EtOAc in heptane to afford 2-(3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenoxy)-2-methyl-propionic acid ethyl ester [0.33 g, 62%, Example 22(a)]. LCMS: RT=2.95 minutes, MS: 466 (M+H). IC50=60 nM
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07517889B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-036b7f206b334b969ce978aac362e5e5 |
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| Source note | uspto-grants-2009_04 |
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