2,6-Dimethylpiperazine → 5-chloro-N-[4-(3,5-dimethylpiperazin-1-yl)-2-methoxyphenyl]-4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-amine

HRID 51

Reaction equation

HRID 51 reaction equation
CC1CNCC(C)N1.COc1cc(Br)ccc1Nc1ncc(Cl)c(-c2cnc3ccccn23)n1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>COc1cc(N2CC(C)NC(C)C2)ccc1Nc1ncc(Cl)c(-c2cnc3ccccn23)n1

Participants

7

Reactant 2

HCID 660562,6-DimethylpiperazineHCID 178418214HCID 178418214, compound

Product 1

HCID 685928185-chloro-N-[4-(3,5-dimethylpiperazin-1-yl)-2-methoxyphenyl]-4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-amineYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 4144353Palladium (II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

N-(4-bromo-2-methoxyphenyl)-5-chloro-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine (107 mg, 0.25 mmol), 2,6-dimethylpiperazine (28.4 mg, 0.25 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.75 mg, 9.94 µmol), diacetoxypalladium (1.116 mg, 4.97 µmol) and cesium carbonate (162 mg, 0.50 mmol) were suspended in 1,4-dioxane (2 mL) . The reaction was purged with nitrogen and heated to 140 °C for 6 hours in an oil bath. Control LC/MS : no traces of expected product.

Sources & evidence

ORD record
ord-d5a89652aac64eea875d9bd85a60b6b2
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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