4-(Tri-n-butylstannyl)pyridine → 4-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-6-pyridin-4-yl-pyrimidine

HRID 965689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 965689
Cl[C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[N:5]=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:23][C:22]1[C:17]([C:13]2[N:12]([CH2:11][C:6]3[C:7]([CH2:8][CH2:9][CH3:10])=[C:2]([C:29]4[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=4)[N:3]=[CH:4][N:5]=3)[CH:16]=[CH:15][N:14]=2)=[N:18][CH:19]=[CH:20][CH:21]=1

Komponenten

5

Edukt 2

HCID 27373184-(Tri-n-butylstannyl)pyridineHCID 100423524-Chloro-6-{[2-(3-fluoro-2-pyridinyl)-1H-imidazol-1-yl]methyl}-5-propylpyrimidine

Produkt 1

HCID 100908044-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-6-pyridin-4-yl-pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine (268 mg, 0.81 mmol), 4-tributylstannanyl-pyridine (1.21 mmol), Pd(PPh3)4 (0.08 mmol, 93 mg) in toluene (10 mL) is degassed. The mixture is then heated at 100° C. overnight. Saturated KF aqueous solution (8 mL) is added and the mixture is stirred for 15 minutes. The layers are separated and the aqueous layer is extracted with EtOAc (10 mL). The combined extracts are washed with brine (15 mL), dried (Na2SO4), and evaporated. Preparative TLC (5% methanol in DCM) purification of the residue provides the title product. 1H NMR (CDCl3) 8.95 (s, 1H), 8.65 (d, 1H), 8.26 (d, 1H), 7.77-7.84 (m, 2H), 7.49 (t, 1H), 7.34 (t, 1H), 7.30 (s, 1H), 7.19-7.22 (m, 1H), 7.14 (s, 1H), 5.92 (s, 2H), 2.87-2.91 (m, 2H), 1.46-1.52 (m, 2H), 0.81 (t, 3H).

Aufarbeitung

  1. customis degassed
  2. additionSaturated KF aqueous solution (8 mL) is added
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (10 mL)
  5. washThe combined extracts are washed with brine (15 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customPreparative TLC (5% methanol in DCM) purification of the residue

Quellen und Nachweise

ORD-Eintrag
ord-d343c5a7b91f4942af61dd211ec110b6
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951864B2

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