HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → (S)-2-(1-((6-Amino-5-(3,5-difluoro-4-hydroxyphenyl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (3,5-Difluoro-4-hydroxyphenyl)boronic acid | HCID 52911287 | — |
| Reactant | HCID 118433733 | HCID 118433733 | — |
| Product | (S)-2-(1-((6-Amino-5-(3,5-difluoro-4-hydroxyphenyl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one | HCID 73776932 | 15.2% |
Reaction Steps
(S)-2-(1-((6-Amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (260 mg, 0.59 mmol) was treated with (3,5-difluoro-4-hydroxyphenyl)boronic acid (154 mg, 0.89 mmol), sodium carbonate (2 M, 1.33 mL, 2.66 mmol) and 2′-(dimethylamino)-2-biphenylyl-palladium(II) chloride dinorbornylphosphine complex (17 mg, 0.03 mmol) according to the method described in the Preparation 17. The residue was purified using SP1® Purification System (0% to 60%, hexane-ethyl acetate) to give 44 mg (15% yield) of the title compound as a white solid. Purity 95%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09388189B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-6cfb8d18c76040fdb7786aa3c5af3d76 |
| Source note | uspto-grants-2016_07 |