1H-Pyrazole-1-carboxylicacid,3-amino-5-methyl-,1,1-dimethylethylester → 4-N-[1-(3,5-difluoro-2-pyridinyl)ethyl]-5-fluoro-2-N-(5-methyl-1H-pyrazol-3-yl)-6-morpholin-4-ylpyrimidine-2,4-diamine

HRID 119Notes

Reaction equation

HRID 119 reaction equation
CC(Nc1nc(Cl)nc(N2CCOCC2)c1F)c1ncc(F)cc1F.Cc1cc(N)nn1C(=O)OC(C)(C)C>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>Cc1cc(Nc2nc(NC(C)c3ncc(F)cc3F)c(F)c(N3CCOCC3)n2)n[nH]1

Participants

7

Reactant 2

HCID 113215371H-Pyrazole-1-carboxylicacid,3-amino-5-methyl-,1,1-dimethylethylesterHCID 78133295HCID 78133295, compound

Product 1

HCID 251030384-N-[1-(3,5-difluoro-2-pyridinyl)ethyl]-5-fluoro-2-N-(5-methyl-1H-pyrazol-3-yl)-6-morpholin-4-ylpyrimidine-2,4-diamineYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (27.9 mg, 0.05 mmol), 2-chloro-N-(1-(3,5-difluoropyridin-2-yl)ethyl)-5-fluoro-6-morpholinopyrimidin-4-amine (200 mg, 0.54 mmol), tert-butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate (127 mg, 0.64 mmol) and cesium carbonate (349 mg, 1.07 mmol) were added to dioxane (8 mL). The mixture was purged with nitrogen for 15 minutes. Pd2(dba)3 (29.4 mg, 0.03 mmol) was added and the mixture heated at 110 °C for 3h. No sign of any reaction.

Sources & evidence

ORD record
ord-20af979b60da4f278f5b92ae2abaf8ca
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

Loading…