Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Triazabicyclodecene | HCID 79873 | — |
| Reactant | 5-Bromo-5-(2-methoxyethyl)pyrimidine-2,4,6(1H,3H,5H)-trione | HCID 21931151 | — |
| Reactant | HCID 22349441 | HCID 22349441 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Diisopropyl Ether | HCID 7914 | — |
| Product | HCID 22349461 | HCID 22349461 | 48% |
Reaction Steps
A mixture of 4-[5-(4-Hydroxy-phenoxy)-indazol-2-yl]-benzonitrile (0.070 grams, 0.22 mmol), 2-methoxyethylbromobarbiturate (0.10 grams, 0.4 mmol), 1,5,7-triazabicyclo[4.4.0]dec-5-ene bound to polystyrene (0.44 grams) and acetonitrile (2.3 mL) was shaken for 24 hours at room temperature. The mixture was treated with a solution of acetic acid in methanol (1:4 v/v), shaken for 20 minutes, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by radial chromatography eluting with 3:2 ethyl acetate-hexanes. Trituration of the purified product with iso-propyl ether afforded 4-(5-{4-[5-(2-Methoxy-ethyl)-2,4,6-trioxo-hexahydro-pyrimidin-5-yloxy]-phenoxy}-indazol-2-yl)-benzonitrile (0.027 grams) as a colorless solid. MS: 512.7 [M+H]+; 510.6 [M−H]−
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06919332B2 |
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| Source dataset | uspto-grants-2005_07 |
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| ORD ID | ord-16de8001ec4e4c1b9464d243517e15f5 |
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| Source note | uspto-grants-2005_07 |
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