Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 4-Methoxybenzylamine | HCID 75452 | — |
| Reactant | HCID 9807724 | HCID 9807724 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 69508536 | HCID 69508536 | 56.1% |
Reaction Steps
(4-Boc-amino-naphthyl)-(2-chloro-6-methyl-pyrimidinyl)-ether (see Example 1) (2.00 g, 5.18 mmol), 4-methoxybenzylamine (0.69 mL, 5.18 mmol) and triethylamine (0.73 mL, 5.18 mmol) were dissolved in 10 mL DMSO in a sealed tube. The tube was sealed and placed into a 95° C. oil bath. The reaction was stirred overnight, then cooled and ethyl acetate and water were added. The aqueous layer was washed twice with EtOAc. The organic extracts were combined, washed once with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was dissolved in dichloromethane and purified by column chromatography on silica gel eluting with EtOAc/hexane, providing 0.625 g of the desired 4-methoxybenzylamino-pyrimidine intermediate as a bright yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07279475B2 |
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| Source dataset | uspto-grants-2007_10 |
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| ORD ID | ord-b53ccaf7170748b8b99eabcb10f8e2b1 |
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| Source note | uspto-grants-2007_10 |
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