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N-Ethylaniline → 5-bromo-N-ethyl-4-methoxy-N-phenylpyrimidin-2-amine

HRID 633
Notes
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Reaction equation

HRID 633 reaction equation
CCNc1ccccc1.COc1nc(I)ncc1Br>CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.CCC(C)(C)[O-].Cc1ccccc1.[Na+].[Pd]>CCN(c1ccccc1)c1ncc(Br)c(OC)n1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 7670N-EthylanilineHCID 848195205-Bromo-2-iodo-4-methoxypyrimidine

Product 1

HCID 1069986935-bromo-N-ethyl-4-methoxy-N-phenylpyrimidin-2-amineYield 70.78%

Reagents, catalysts & solvents 4

HCID 2733478Sodium 2-methylbutan-2-olateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
Catalyst
HCID 4144353Palladium (II) acetateCatalyst
HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

5-bromo-2-iodo-4-methoxypyrimidine (0.086 g, 0.27 mmol), diacetoxypalladium (2.78 mg, 0.01 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) - XantPhos (7.16 mg, 0.01 mmol) and sodium 2-methylbutan-2-olate (0.055 g, 0.50 mmol) and di((3S,5S,7S)-adamantan-1-yl)(butyl)phosphine (8.88 mg, 0.02 mmol) were added to a micro vial. Then N-ethylaniline (0.031 mL, 0.25 mmol) in toluene (1.5 mL) was added to the reaction mixture. The vial was sealed and evacuated and flushed with nitrogen and then stirred at 100°C o/n. LC/MS showed product formation. The reaction mixture was cooled to rt and then filtered over celite. The crude product was diluted with 25 ml of DCM and then washed with sat. NaHCO3 followed by brine. The organic phase was dried over a phase separator and then concentrated to dryness. **No LC/MS data due to database failure over three months and was only saved locally on LC/MS computer and pdf-files seems to be deleted on machine. Not used in further reactions.**

Sources & evidence

ORD record
ord-3df00475fe9d41898bd3503e3b2ed03d
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes