HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1907783Generated: October 31, 2026
4-Aminopyrimidine → 6-Chloro-3-methoxy-N-(pyrimidin-4-yl)pyridazin-4-amine
https://huagongshe.com/reaction/1907783
Participants
| Role | Name | HCID | Charge |
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| Reactant | 4-Aminopyrimidine | HCID 68958 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Phenolate Sodium | HCID 4445035 | — |
| Reactant | 6-Chloro-4-iodo-3-methoxypyridazine | HCID 23092481 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | 6-Chloro-3-methoxy-N-(pyrimidin-4-yl)pyridazin-4-amine | HCID 58540288 | — |
Reaction Steps
In a dried pressure flask was placed compound 2 (1.0 g, 3.70 mmol), 4-aminopyrimidine (352 mg, 3.7 mmol), sodium phenoxide (860 mg, 7.4 mmol), Pd2(dba)3 (170 mg, 5 mol %), and Xantphos (150 mg, 7 mol %). The flask was evacuated and filled with N2 3× and then 20 mL anhydrous dioxane was added, The mixture was heated at 100° C. for 12 hours. The cooled mixture was diluted with ethyl acetate and water, filtered, separated, the ethyl acetate layer extracted 1× with ethyl acetate, the combined ethyl acetate layers washed with brine 4×, dried over Na2SO4, filtered and concentrated. The product was purified by column chromatography (silica) CH2Cl2/MeOH to give 3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08598174B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-aa5417eaa2844ebf89d9d77360464d84 |
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| Source note | uspto-grants-2013_12 |
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