Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-(Pyrimid-5-ylmethyl)-2-thiouracil | HCID 10966039 | — |
| Reactant | 4-(Chloromethyl)phenyl 4-chloro-3-(trifluoromethyl)phenyl ether | HCID 66825537 | — |
| Catalyst | Zinc bromide | HCID 10421208 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 67776141 | HCID 67776141 | 7.3% |
Reaction Steps
To a solution of 5-(5-pyrimidinylmethyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (70 mg, 0.318 mmol) and DIPEA (0.083 ml, 0.477 mmol) in DCM (2 ml) was added 1-chloro-4-{[4-(chloromethyl)phenyl]oxy}-2-(trifluoromethyl)benzene (110 mg, 0.343 mmol). The reaction mixture was heated at 60° C. overnight. After removing the solvent by nitrogen, the residue was dissolved in MeCN (4 ml), and NMP (1.5 ml), and ZnBr2 (107 mg, 0.477 mmol) and DIPEA (0.083 ml, 0.477 mmol) were added. The mixture was then stirred at 60° C. for 10 min and MeI (0.020 ml, 0.318 mmol) was added dropwise, then stirred at 60° C. for 1.5 h. Purification via MDAP then afforded the title compound (12 mg, 5.97% yield). LCMS: rt=3.38 min, [M+H+]=519
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08637536B2 |
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| Source dataset | uspto-grants-2014_01 |
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| ORD ID | ord-bfbd3bbb7f1a4b40b7b4bde3338181b2 |
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| Source note | uspto-grants-2014_01 |
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