HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2200496Generated: October 31, 2026
p-Toluidine → tert-butyl (3R,4R)-4-(5-cyano-6-(p-tolylamino)pyrazin-2-ylamino)tetrahydro-2H-pyran-3-ylcarbamate
https://huagongshe.com/reaction/2200496
Participants
| Role | Name | HCID | Charge |
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| Reactant | p-Toluidine | HCID 7813 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | tert-butyl (3R,4R)-4-(6-chloro-5-cyanopyrazin-2-ylamino)tetrahydro-2H-pyran-3-ylcarbamate | HCID 86685613 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | tert-butyl (3R,4R)-4-(5-cyano-6-(p-tolylamino)pyrazin-2-ylamino)tetrahydro-2H-pyran-3-ylcarbamate | HCID 86685614 | 44.6% |
Reaction Steps
To a mixture of tert-butyl (3R,4R)-4-(6-chloro-5-cyanopyrazin-2-ylamino)tetrahydro-2H-pyran-3-ylcarbamate (100 mg, 0.28 mmol) in Dioxane (2 mL) was added p-toluidine (37 mg, 0.35 mmol), Pd(OAc)2 (13 mg, 0.056 mmol), BINAP (35 mg, 0.056 mmol) and K2CO3 (116 mg, 0.84 mmol). After heating at 95° C. for 4 h, the mixture was filtered, the filtrate was concentrated and purified by preparative HPLC to give tert-butyl (3R,4R)-4-(5-cyano-6-(p-tolylamino)pyrazin-2-ylamino)tetrahydro-2H-pyran-3-ylcarbamate (53 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09359308B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-2189705d7bfb4d7fa2cf523a9b24bebf |
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| Source note | uspto-grants-2016_06 |
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