Dimethyl Sulfoxide → 6-{[(4-chloro-phenyl)-methyl-amino]-methyl}-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

HRID 271553

Reaktionsgleichung

Reaktionsgleichung von HRID 271553
Br[CH2:2][C:3]1[N:13]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]2[N:7]=[C:8]([C:11]#[N:12])[N:9]=[CH:10][C:5]=2[CH:4]=1.CS(C)=O.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([NH:28][CH3:29])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O.CCCCCC>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([N:28]([CH2:2][C:3]2[N:13]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]3[N:7]=[C:8]([C:11]#[N:12])[N:9]=[CH:10][C:5]=3[CH:4]=2)[CH3:29])=[CH:26][CH:25]=1

Komponenten

8

Edukt 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 702724-Chloro-N-methylbenzenamineHCID 113128256-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

Produkt 1

HCID 101770306-{[(4-chloro-phenyl)-methyl-amino]-methyl}-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrileAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 6-bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (1 mmol) in DMF (or DMSO) (5 ml) are added 4-chloro-N-methylaniline (1.2 mmol) and potassium carbonate (2.4 mmol). The mixture is heated at 50° C. for 13 h. The reaction mixture is diluted with AcOEt, washed with water and brine, dried over sodium sulfate and concentrated. The crude product is purified by HPLC (n-hexane:AcOEt) to give the product in 27% yield. Rf=0.69(n-hexane:AcOEt=1:1). 1H NMR(400 MHz, CDCl3) δ 1.06(s, 9H), 3.03(s, 3H), 4.13(s, 2H), 4.71(s, 2H), 6.40(s, 1H), 6.62-6.69(m, 2H), 7.17-7.23(m, 2H), 8.84(s, 1H).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product is purified by HPLC (n-hexane:AcOEt)
  5. customto give the product in 27% yield

Quellen und Nachweise

ORD-Eintrag
ord-846a310dddb142d1968582f1dd6e3500
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452886B2

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