Triethylamine → 6-(4-methoxybenzyl)-7-neopentyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

HRID 271596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271596
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[CH:11])=[CH:5][CH:4]=1.Br[C:13]1[C:14]([NH:21][CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:15][C:16]([C:19]#[N:20])=[N:17][CH:18]=1.C(N(CC)CC)C>CN(C=O)C.O.[Cu]I.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>[CH3:24][C:23]([CH3:26])([CH3:25])[CH2:22][N:21]1[C:14]2[N:15]=[C:16]([C:19]#[N:20])[N:17]=[CH:18][C:13]=2[CH:11]=[C:10]1[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 107731151-Methoxy-4-(prop-2-yn-1-yl)benzeneHCID 179681615-Bromo-4-(2,2-dimethylpropylamino)pyrimidine-2-carbonitrile

Produkt 1

HCID 444442086-(4-methoxybenzyl)-7-neopentyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1-Methoxy-4-prop-2-ynyl-benzene (3.01 mmol) is dissolved in DMF (7 ml) at room temperature under nitrogen atmosphere. To the solution, 5-bromo-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile (2.01 mmol), triethylamine (6 mmol), copper(I) iodide (0.2 mmol), and dichlorobis(triphenylphosphine)palladium (II) (0.1 mmol) are added successively. The mixture is heated at 80° C. under nitrogen atmosphere for 3 h. After cooling at room temperature, the mixture is diluted with H2O and extracted with AcOEt. The organic layer is dried over MgSO4 and evaporated in vacuo. The residue is purified by silica gel column chromatography (n-hexane:AcOEt=7:1) to give 7-(2,2-dimethyl-propyl)-6-(4-methoxy-benzyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 57%.

Aufarbeitung

  1. temperatureAfter cooling at room temperature
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer is dried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue is purified by silica gel column chromatography (n-hexane:AcOEt=7:1)

Quellen und Nachweise

ORD-Eintrag
ord-6ce55ff99c944b998dfe848fc8410022
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452886B2

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