Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Picolinoyl Chloride Hydrochloride | HCID 135033 | — |
| Reactant | 5-(4-amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine | HCID 22736344 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 22736418 | HCID 22736418 | — |
Reaction Steps
5-(4-Amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (80mg, 0.236 mmol) was dissolved in dichloromethane (2.0 mL). Pyridine (2.0 mL) was added followed by 2-pyridinecarbonyl chloride hydrochloride (63 mg, 0.353 mmol). After stirring at room temperature for 2 hours, the solvent was removed and the residue was dissolved in 1 ml DMSO, methanol (1 mL) was added and precipitate was formed. The solid was collected by filtration to give N5-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-1,3-dimethyl-1H-5-pyrazolecarboxamide (30 mg, 0.065 mmol). 1H NMR (CDCl3-d) δ 2.11 (m, 4H), 2.32 (s, 3H), 3.66 (m, 2H), 3.99 (s, 3H), 4.13(m, 2H), 4.17 (s, 3H), 4.99 (m, 1H), 5.22 (bs, 2H), 6.46 (s, 1H), 7.03 (s, 1H), 7.07 (s, 1H), 7.12 (d, J=8.2 Hz, 1H), 8.33 (2, 2H), 8.49(d, J=8.2 Hz, 1H). LC/MS: MH+=462.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06713474B2 |
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| Source dataset | uspto-grants-2004_03 |
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| ORD ID | ord-f5aa93bacd9f4874b776131f44196992 |
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| Source note | uspto-grants-2004_03 |
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