Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1,3-Dibromo-2-propanone | HCID 69952 | — |
| Reactant | N-(5-Bromopyridin-2-yl)thiourea | HCID 23438874 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 25260860 | HCID 25260860 | 16% |
Reaction Steps
(5-Bromo-pyridine-2-yl)-thiourea (2.5 mmol) is dissolved in DMF (5 ml) and 1,3-dibromacetone (1 eq.) is added and stirred 2 h at 70° C. After cooling to RT, the reaction solution is poured into water and the resulting precipitate is filtered, washed with water and dried 16 h in vacuo at 40° C. After column chromatography (ethyl acetate/methanol) (4-bromomethyl-thiazole-2-yl)-(5-bromo-pyridine-2-yl)-amine is obtained as a colourless powder with a yield of 16%. HPLC (method C): 1.92 min; LC-MS (method A): 1.977 min, 347.95 (M+H+); 1H-NMR (DMSO-d6, 300 MHz): δ [ppm] 11.583 (s, 1H), 8.391 (d, 1H, J=2.4 Hz), 7.902 (dd, 1H, J=2.4 Hz, J=8.9 Hz), 7.119 (s, 1H), 7.023 (d, 1H, J=8.9 Hz), 4.622 (s, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08420642B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-d37a82a3816f4c21a7e904062e6d3465 |
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| Source note | uspto-grants-2013_04 |
|---|