Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,4-Dichloro-5-nitropyrimidine | HCID 521266 | — |
| Reactant | (R)-2-Amino-2-(4-fluorophenyl)ethanol | HCID 10583003 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 86630702 | HCID 86630702 | 29% |
Reaction Steps
To a solution of 2,4-dichloro-5-nitropyrimidine (1.5 g, 7.73 mmol) in EtOH (25 ml) at 0° C. was added triethylamine (1.6 ml, 11.6 mmol) and a solution of (2R)-2amino-2-(4-fluorophenyl)ethanol (prepared according to a procedure in J. Med. Chem. 1999, 42, 4981-5001, 1.2 g, 7.73 mmol). The reaction mixture was stirred at 0° C. for 3 hours. The solvent was removed and the residue was dissolved in EtOAc and was washed with water. The organic layer was concentrated. Flash chromatography on silica gel (20-50% EtOAc in hexanes) gave the title compound as a solid (703 mg, 29%). NMR (CDCl3) 4.00 (m, 2H), 5.50 (m, 1H), 7.07 (m, 2H), 7.38 (m, 2H), 9.04 (s, 1H), 9.10 (br s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07622482B2 |
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| Source dataset | uspto-grants-2009_11 |
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| ORD ID | ord-6c3c8f2a9f9046c3b6603f9f5cc7ccb4 |
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| Source note | uspto-grants-2009_11 |
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