Triethylamine → 6-[(1-Methyl-4-phenyl-1H-imidazol-5-yl)ethynyl]pyrimidine-4,5-diamine

HRID 32603

Reaktionsgleichung

Reaktionsgleichung von HRID 32603
I[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].[C:10]([C:12]1[N:16]([CH3:17])[CH:15]=[N:14][C:13]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)#[CH:11].C(N(CC)CC)C>CN(C=O)C.[Cu]I>[CH3:17][N:16]1[C:12]([C:10]#[C:11][C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=2[NH2:9])=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]=[CH:15]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 179658065-Ethynyl-1-methyl-4-phenyl-1H-imidazole2×HCID 179658946-Iodopyrimidine-4,5-diamine2×

Produkt 1

HCID 179657996-[(1-Methyl-4-phenyl-1H-imidazol-5-yl)ethynyl]pyrimidine-4,5-diamineAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Iodopyrimidine-4,5-diamine (Intermediate 89) (50 mg), CuI (2 mg), PdCl2dppf (16 mag), 5-ethynyl-1-methyl-4-phenyl-1H-imidazole (intermediate 26) (77 mg), and triethylamine (0.33 mL) in DMF (7 mL) were mixed together and then degassed. The reaction mixture was allowed to stir at ambient temperature under an inert atmosphere for 24 hours. The reaction mixture was filtered through diatomaceous earth, washing well with DCM and then MeCN. The organics were concentrated and the residue purified by chromatography on silica eluting with DCM:MeOH (9:1) to afford the title compound as a yellow solid (47 mg, 76%);

Aufarbeitung

  1. customdegassed
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. washwashing well with DCM
  4. concentrationThe organics were concentrated
  5. customthe residue purified by chromatography on silica eluting with DCM:MeOH (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-d720884f28ce43b4bd80e03c3ddae8c0
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427616B2

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