HuagongsheHuagongshe Chemistry Print Report · For research reference only
HCID 58169125, compound → 3-(tert-butyldimethylsilyloxy)-3-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-yl)propyl acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | HCID 58169125 | HCID 58169125 | — |
| Reactant | 5-(3-Acetoxy-1-(tert-butyldimethylsilyloxy)propyl)thiophen-2-ylboronic acid | HCID 58169148 | — |
| Reactant | Ethyl 2-(5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophen-2-yl)-2-hydroxyacetate | HCID 58169421 | — |
| Reactant | HCID 58169522 | HCID 58169522 | — |
| Product | 3-(tert-butyldimethylsilyloxy)-3-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-yl)propyl acetate | HCID 58169548 | 50% |
Reaction Steps
Following procedure from Compound 191, 3-(5-Bromothiophen-2-yl)-3-(tert-butyldimethylsilyloxy)propyl acetate was converted to 5-(3-acetoxy-1-(tert-butyldimethylsilyloxy)propyl)thiophen-2-ylboronic acid (2.7 g, 94.5%) (LC-MS (m/z)=441.0 [M+H]+), which was condensed with 2-bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine to produce 3-(tert-butyldimethylsilyloxy)-3-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-yl)propyl acetate (500 mg, 50.0%). LC-MS (m/z)=538.1 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09422271B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-f2ecd5a280de45c8852295772ed164ba |
| Source note | uspto-grants-2016_08 |