HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diethylamine → 5-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-pent-4-ynoic acid diethylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diethylamine | HCID 8021 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 5-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-pent-4-ynoic acid | HCID 57713842 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | 5-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-pent-4-ynoic acid diethylamide | HCID 11950888 | — |
Reaction Steps
A mixture of 5-[2-amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo [2,3-d]pyrimidin-5-yl]-pent-4-ynoic acid (see previous example, 25 mg), Et2NH (100 μL), EDCI (87 mg), HOBt (50 mg), and DMF (1 mL) was stirred at rt for 16 h. Preparative plate chromatography (EtOAc/hexane 2:1) gave the title compound. tR=5.33 min. 1H NMR (CDCl3) δ 8.23 (s, 1H), 7.01 (s, 1H), 5.32 (s, 2H), 4.98 (s, 2H), 3.76 (s, 3H), 3.42 (q, 2H), 3.33 (q, 2H), 2.78 (dd, 2H), 2.64 (dd, 2H), 2.27 (s, 3H), 2.18 (s, 3H), 1.20 (t, 3H), 1.13 (t, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08093229B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-bfbdc9adf803467cbac220f966ab678c |
| Source note | uspto-grants-2012_01 |