HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(2-Amino-ethyl)-2-chloro-phenol hydrobromide salt → tert-Butyl-(3-{2-[2-(3-chloro-4-hydroxy-phenyl)-ethylamino]pyrimidin-4-yl}-benzyl)-carbamic acid allyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(2-Amino-ethyl)-2-chloro-phenol hydrobromide salt | HCID 67045103 | — |
| Reactant | tert-Butyl-[3-(2-chloro-pyrimidin-4-yl)-benzyl]-carbamic acid allyl ester | HCID 86603311 | — |
| Product | tert-Butyl-(3-{2-[2-(3-chloro-4-hydroxy-phenyl)-ethylamino]pyrimidin-4-yl}-benzyl)-carbamic acid allyl ester | HCID 67045639 | 79% |
Reaction Steps
tert-Butyl-[3-(2-chloro-pyrimidin-4-yl)-benzyl]-carbamic acid allyl ester was coupled with 4-(2-amino-ethyl)-2-chloro-phenol hydrobromide salt (intermediate 71) following procedure F to give the title product in 79% yield. LC-MS showed the product had the expected M+H+ of 495. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) 8.3 (d, 1H)) 7.9 (m, 2H) 7.4 (m, 1H) 7.3 (m, 1H) 7.2 (s, 1H) 7.0 (d, 1H) 6.9 (m, 2H) 5.9 (m, 1H) 5.2 (m, 2H) 5.1 (m, 2H) 4.7 (s, 2H) 4.6 (d, 2H) 3.7 (m, 2H) 2.9 (m, 2H) 1.41 (s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08268822B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-c4f060b7e2534caa8b16b02b5ec99758 |
| Source note | uspto-grants-2012_09 |