4,6-Dichloropyrimidine → 5-(6-Chloropyrimidin-4-ylamino)-3-methoxypyrazine-2-carbonitrile

HRID 556882

Reaktionsgleichung

Reaktionsgleichung von HRID 556882
[NH2:1][C:2]1[N:3]=[C:4]([O:10][CH3:11])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[Cl:12][C:13]1[CH:18]=[C:17](Cl)[N:16]=[CH:15][N:14]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:12][C:13]1[N:14]=[CH:15][N:16]=[C:17]([NH:1][C:2]2[N:3]=[C:4]([O:10][CH3:11])[C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH:18]=1

Komponenten

7

Edukt 4

HCID 709434,6-DichloropyrimidineHCID 2733832Lithium HexamethyldisilazideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 596133845-Amino-3-methoxypyrazine-2-carbonitrile

Produkt 1

HCID 596135175-(6-Chloropyrimidin-4-ylamino)-3-methoxypyrazine-2-carbonitrileAusbeute 28,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

5-Amino-3-methoxypyrazine-2-carbonitrile (9.2 mg, 0.061 mmol), 4,6-dichioropyrimidine (10 mg, 0.067 mmol), lithium bis(trimethylsilyl)amide (1M, 75 uL, 0.075 mmol), Pd2(dba)3 (3.5 mg, 5.5% mol) and 2-(di-tert-butyl-phosphino)biphenyl (2 mg, 0.0067 mmol) were mixed in THF (0.5 mL). The reaction mixture was heated at 135° C. for 60 minutes using microwave irradiation. The crude product was purified by preparative thin layer chromatography, eluting with EtOAc/n-hexane (1/2), to give the title compound as an oil (4.5 mg, 28%).

Aufarbeitung

  1. custommicrowave irradiation
  2. customThe crude product was purified by preparative thin layer chromatography
  3. washeluting with EtOAc/n-hexane (1/2)

Quellen und Nachweise

ORD-Eintrag
ord-0b79adca44f747178bd0d71a28cf9618
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058045B2

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