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

HRID 633
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 633
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
KomponentenReaktionsbedingungenVersuchsvorschriftQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 2

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

Produkt 1

HCID 1069986935-bromo-N-ethyl-4-methoxy-N-phenylpyrimidin-2-amineAusbeute 70,78 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2733478Sodium 2-methylbutan-2-olateReagenzHCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
Katalysator
HCID 4144353Palladium (II) acetateKatalysator
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.**

Quellen und Nachweise

ORD-Eintrag
ord-3df00475fe9d41898bd3503e3b2ed03d
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
Quelle ansehen

Notizen zur Reaktion

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