Triethylamine → {4-[2-Cyano-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl]-phenyl}-methanesulfonamide

HRID 271601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271601
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([NH2:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1)[C:2]#[CH:3].Br[C:16]1[C:17]([NH:24][CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[N:18][C:19]([C:22]#[N:23])=[N:20][CH:21]=1.C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:22]([C:19]1[N:20]=[CH:21][C:16]2[CH:3]=[C:2]([CH2:1][C:4]3[CH:9]=[CH:8][C:7]([CH2:10][S:11]([NH2:14])(=[O:12])=[O:13])=[CH:6][CH:5]=3)[N:24]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:17]=2[N:18]=1)#[N:23]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 179681615-Bromo-4-(2,2-dimethylpropylamino)pyrimidine-2-carbonitrileHCID 86628141(4-Prop-2-ynyl-phenyl)-methanesulfonamide

Produkt 1

HCID 86628142{4-[2-Cyano-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl]-phenyl}-methanesulfonamideAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of N.-(4-prop-2-ynyl-phenyl)-methanesulfonamide (1.0 mmol) and 5-bromo-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile (0.5 mmol) in DMF (5 ml), triethylamine (1.5 mmol), dichlorobis-dichlorobis(triphenylphosphine)palladium (II) (0.05 mmol) and copper (I) iodide (0.1 mmol) is added. The reaction mixture is heated at 70° C. ca. for 2.5 h. The mixture is quenched with saturated ammonium chloride and extracted with two 50 ml portions of AcOEt. The combined extracts are washed with brine, dried over sodium sulfate and concentrated under vacuum to give crude product, which is purified by silica gel column chromatography. Yield: 60.7%. Rf=0.55 (n-hexane:AcOEt=1:1)

Aufarbeitung

  1. customThe mixture is quenched with saturated ammonium chloride
  2. extractionextracted with two 50 ml portions of AcOEt
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto give crude product, which
  7. customis purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a277a49d03464a02a2d58eacd3a41ef1
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452886B2

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