Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triphenylarsine | HCID 11773 | — |
| Reactant | 2-(Tri-n-butylstannyl)oxazole | HCID 15486183 | — |
| Reactant | 2-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile | HCID 18753230 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 18507230 | HCID 18507230 | 8.1% |
Reaction Steps
To a stirred solution of 2.37 g (9.67 mmol) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile in 50 ml dry DMF under argon at room temperature were added 4.50 g (12.6 mmol) 2-tributylstannanyl-oxazole, 889 mg (0.97 mmol) tris(dibenzylidene-acetone)dipalladium(O), 1.48 g (4.84 mmol) triphenylarsine and 185 mg (0.97 mmol) copper(I) iodide. The reaction mixture was heated at 95° C. for 48 h, then cooled to room temperature and partitioned between ethyl acetate and water. The phases were separated and the organic phase dried over sodium sulfate and concentrated in vacuo. Flash chromatography (ethyl acetate/hexane 1/1 followed by ethyl acetate) afforded 182 mg (7%) 2-amino-4-methylsulfanyl-6-oxazol-2-yl-pyrimidine-5-carbonitrile as a yellow crystalline solid. ES-MS m/e (%): 234 (M+H+, 100).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06586441B2 |
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| Source dataset | uspto-grants-2003_07 |
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| ORD ID | ord-8ff21769ec9d4df5a80d4798002010a2 |
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| Source note | uspto-grants-2003_07 |
|---|
