Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4,5-Dichloro-6-ethylpyrimidine | HCID 11137668 | — |
| Reactant | HCID 15376258 | HCID 15376258 | — |
| Reactant | HCID 20498269 | HCID 20498269 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 15376259 | HCID 15376259 | — |
Reaction Steps
2.4 g (13.5 mmol) of 4,5-dichloro-6-ethylpyrimidine, 2.4 g (13.5 mmol) of 5-amino-2-phenyltetrahydropyran (prepared from 2-phenyltetrahydropyran-5-ol (cf. U.S. Pat. No. 4,388,104) analogously to the routes described in Example A) and 3 ml (21 mmol) of triethylamine were heated for 12 hours at 85° C. After cooling, the mixture was diluted with water and extracted with ether, and the organic phase was washed with saturated NaCl solution. After drying and concentrating, the residue was purified by column chromatography using petroleum ether/ethyl acetate (9:1, 8:2). This gave 0.65 g (15% of theory) of the trans isomer as a colorless oil and 2.17 g (51% of theory) of the cis isomer as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06207668B1 |
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| Source dataset | uspto-grants-2001_03 |
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| ORD ID | ord-3d320e174bfa45989fcdd837f478be03 |
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| Source note | uspto-grants-2001_03 |
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