Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Chloro-6-ethyl-5-fluoropyrimidine | HCID 16743445 | — |
| Reactant | 1H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)- | HCID 67111459 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 70944643 | HCID 70944643 | — |
Reaction Steps
A solution of 1-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 50 mg, 0.232 mmol) in dry NMP (2 mL) was treated with 4-chloro-6-ethyl-5-fluoropyrimidine (Intermediate 27, 74.6 mg, 0.465 mmol) and DIPEA (0.081 mL, 0.465 mmol). The reaction mixture was then stirred at room temperature over the weekend. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (20 mL). The organic extract was then washed with water (20 mL×2), dried (MgSO4), filtered and the solvent was removed. The resulting residues were then purified on the MDAP and fractions containing desired product were combined and evaporated to dryness. The resulting residues were then dissolved in methanol (10 mL) and 4M HCl in dioxane (1 mL) was added. The mixture was then evaporated to dryness to give the title compound as an off white solid (45 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796283B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-2a61fc83e7c541e6a9e4e8ac67d2ac15 |
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| Source note | uspto-grants-2014_08 |
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