HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-Iodosuccinimide → N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-Iodosuccinimide | HCID 120273 | — |
| Reactant | N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide | HCID 11425285 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide | HCID 15484841 | 81% |
Reaction Steps
A solution of N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide (101 g, 0.40 mol) in anhydrous THF (2 L) was treated with N-iodosuccinimide (98.9 g, 0.44 mol, 1.1 eq.) under N2 atmosphere at rt for 40 min. The solvent was evaporated, and the residue was taken up in CH2Cl2 (1.5 L), and washed with Na2SO3 (500 mL×3) and brine (300 mL×3). Evaporated and recrystallizion from MeOH gave the title product as a white powder (122 g, 81% yield, HPLC purity: 98.2%). tR: 6.19 min. 1H-NMR (DMSO-d6) δ 12.65 (br.s, 1H), 10.11 (br. s, 1H), 7.76 (d, 1H), 1.24 (s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07544672B2 |
| Source dataset | uspto-grants-2009_06 |
| ORD ID | ord-f2f2d28c2b15465fbbf82eb51a194c16 |
| Source note | uspto-grants-2009_06 |