(2S)-2-aminopentan-1-ol → 2-[4-[[2-amino-4-[[(2S)-1-hydroxypentan-2-yl]amino]-6-methylpyrimidin-5-yl]methyl]phenyl]acetonitrile

HRID 87

Reaction equation

HRID 87 reaction equation
CCC[C@H](N)CO.Cc1nc(N)nc(Cl)c1Cc1ccc(CC#N)cc1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[K+].[K+].[Pd]>CCC[C@@H](CO)Nc1nc(N)nc(C)c1Cc1ccc(CC#N)cc1

Participants

7

Reactant 2

HCID 6951248(2S)-2-aminopentan-1-olHCID 874447822-(4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)phenyl)acetonitrile

Product 1

HCID 689557742-[4-[[2-amino-4-[[(2S)-1-hydroxypentan-2-yl]amino]-6-methylpyrimidin-5-yl]methyl]phenyl]acetonitrileYield 0%

Reagents, catalysts & solvents 4

HCID 11430Potassium CarbonateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 4144353Palladium (II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Palladium(II) acetate (8.23 mg, 0.04 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (42.4 mg, 0.07 mmol) were added to dioxane (3 mL) and the solution was stirred at room temperature for 10 minutes. 2-(4-((2-amino-4-chloro-6-methylpyrimidin-5-yl)methyl)phenyl)acetonitrile (200 mg, 0.73 mmol), (S)-(+)-2-Amino-1-pentanol (151 mg, 1.47 mmol) and POTASSIUM CARBONATE (203 mg, 1.47 mmol) were added and the mixture was heated at 100 °C for 15 hours. LCMS showed no product and reaction not progressed.

Sources & evidence

ORD record
ord-d1855bc74886445fbdfc0eab57bed8cb
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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