Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Bromothiazole | HCID 76430 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (2,4-Dimethoxypyrimidin-5-yl)boronic acid | HCID 2736209 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 59448375 | HCID 59448375 | — |
Reaction Steps
2-bromo-1,3-thiazole (commercially available from Aldrich, 0.165 ml, 1.829 mmol) was dissolved in degassed 1,2-Dimethoxyethane (DME) (5 ml). Pd(Ph3)4 (106 mg, 0.091 mmol) was added. The reaction mixture was stirred at room temperature for 15 min. [2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid (commercially available from Aldrich, 707 mg, 3.84 mmol) and 5 mL of degassed 1M aqueous solution of NaHCO3 were added to the reaction mixture under N2 atmosphere. After 2 h 30 min stirring at 90° C., the reaction mixture was diluted with water and extracted with DCM. The collected organic phases were evaporated. The residue was purified by flash chromatography eluting with cyclohexane/EtOAc 5:1. 294 mg of the title compound were isolated as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08178549B2 |
|---|
| Source dataset | uspto-grants-2012_05 |
|---|
| ORD ID | ord-52b7ba7c53c74b49840acd4e066398c3 |
|---|
| Source note | uspto-grants-2012_05 |
|---|