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HRID19

Reaction detail

2 reactants → 1 products · 2 catalysts Palladium、1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) · 1 solvents Toluene · 110 °C

EQUATION

Reaction equation

HRID 19 reaction equation

Participants

7

Reactant 2

5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine molecular structure
HCID16665498

5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine

C13H16FN5O

4-(4-Bromo-3-fluorobenzyl)morpholine molecular structure
HCID53417818

4-(4-Bromo-3-fluorobenzyl)morpholine

C11H13BrFNO

Product 1

5-Fluoro-N-(2-fluoro-4-(morpholinomethyl)phenyl)-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine molecular structure
HCID49782013

5-Fluoro-N-(2-fluoro-4-(morpholinomethyl)phenyl)-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine

C24H28F2N6O2

Yield 85%

Reagents, catalysts & solvents 4

Sodium 2-methylbutan-2-olate molecular structure
ReagentHCID2733478

Sodium 2-methylbutan-2-olate

C5H11NaO

Palladium molecular structure
CatalystHCID23938

Palladium

Pd

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) molecular structure
CatalystHCID636044

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

C39H32OP2

Toluene molecular structure
SolventHCID1140

Toluene

C7H8

Conditions

Temperature
110 °C

Procedure

The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (94 mg, 0.16 mmol) and Sodium tert-pentoxide (79 mg, 0.72 mmol) were dissolved in toluene (1.5 mL) and heated to 110 °C under argon. The reaction was monitorred by HPLC. After 16 h 85 % conversion was achieved. The reaction was stopped and the mixture was discarded.

Sources & evidence

ORD recordord-ea29507936c14849a1aa88403efb7090
Source dataset750 AstraZeneca ELN dataset
Original linkView source

NOTES

Linked notes

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