Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | 2-Amino-4,6-dichloropyrimidine | HCID 65522 | — |
| Reactant | 1H-Imidazole-4-carbaldehyde | HCID 76428 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Catalyst | Titanium isopropoxide | HCID 11026 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178478190 | HCID 178478190 | 26% |
Reaction Steps
To a solution of 2-amino-4,6-dichloropyrimidine (1.00 g, 7.72 mmol) in dichloromethane (8 ml) were added 4-formylimidazole (0.74 g, 7.72 mmol) and tetraisopropyl orthotitanate (2.86 ml, 9.65 mmol). After stirring the mixture at 40° C. overnight ethanol (8 ml) and sodium borohydride (0.38 g, 10.0 mmol) were added. The reaction mixture was stirred 40° C. for 7 hours. Then mixture was concentrated in vacuo and the residue was purified by flash chromatography (methanol/dichloromethane gradient) to yield white crystals (43 mg, 26%); MS (EI): 247.1 (37Cl M+.), 245.1 (37Cl35Cl M+.), 243.1 (35Cl M+.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08586617B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-b1651686212e42da858c6c83d723b07d |
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| Source note | uspto-grants-2013_11 |
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