Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 67175825 | HCID 67175825 | — |
| Reactant | HCID 67175878 | HCID 67175878 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58382522 | HCID 58382522 | — |
| Product | HCID 58382524 | HCID 58382524 | — |
Reaction Steps
91.5 mg of morpholine and 207 mg of potassium carbonate were added to a solution of 169 mg of the mixture of 5-bromomethyl-2-furan-2-yl-7-propoxy-oxazolo[5,4-d]pyrimidine and 2-(5-bromo-furan-2-yl)-5-bromomethyl-7-propoxy-oxazolo[5,4-d]pyrimidine obtained in step (a) in 3 ml of dimethylformamide. The reaction mixture was stirred at room temperature for 48 h. Then 50 ml each of water and ethyl acetate were added, the mixture was filtered through a Varian ChemElut cartridge, the cartridge washed with 10 ml of ethyl acetate, and the combined filtrates were evaporated to dryness in vacuo. Preparative HPLC (method HPLC1) of the residue yielded 41 mg of 2-(5-bromo-furan-2-yl)-5-morpholin-4-ylmethyl-7-propoxy-oxazolo[5,4-d]pyrimidine (example 3) and 25 mg of the title compound in the form of 2-furan-2-yl-5-morpholin-4-ylmethyl-7-propoxy-oxazolo[5,4-d]pyrimidine trifluoroacetic acid salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08735387B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-1a1c3a51a45e48c4934be435e9fae2f9 |
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| Source note | uspto-grants-2014_05 |
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