3-(2,5-Dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine → N-(4-(azetidin-3-yloxy)-2-methoxyphenyl)-5-chloro-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine

HRID 64

Reaction equation

HRID 64 reaction equation
COc1cc(OC2CN(C(=O)OC(C)(C)C)C2)ccc1N.Clc1ncc(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(OC2CNC2)ccc1Nc1ncc(Cl)c(-c2cnc3ccccn23)n1

Participants

7

Reactant 2

HCID 469346053-(2,5-Dichloropyrimidin-4-yl)imidazo[1,2-a]pyridineHCID 59291149Tert-butyl 3-(4-amino-3-methoxyphenoxy)azetidine-1-carboxylate

Product 1

HCID 45381546N-(4-(azetidin-3-yloxy)-2-methoxyphenyl)-5-chloro-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidin-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
105 °C

Procedure

3-(2,5-dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine (100 mg, 0.38 mmol) _,_ tert-butyl 3-(4-amino-3-methoxyphenoxy)azetidine-1-carboxylate (111 mg, 0.38 mmol) _,_ CESIUM CARBONATE (246 mg, 0.75 mmol) _,_ diacetoxypalladium (3.39 mg, 0.02 mmol) _and_ 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (17.46 mg, 0.03 mmol) ___were_ ___suspended_ _in_ 1,4-dioxane (1 ml) _and degased with argon.The reaction was heated from 60°C to 105°C for 3 hours.Doubt about the LCMS,deprotection of the BOC with TFA to confirm the dialkylation._ No good product

Sources & evidence

ORD record
ord-297038d2636048ff93bf3571d541a46e
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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