Dimethylamine → 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide

HRID 2189315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2189315
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([C:11]([OH:13])=O)[N:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:6]=2[N:7]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)[N:37]([CH3:39])[CH3:38])C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.CNC>CN(C=O)C.C1COCC1>[CH3:38][N:37]([CH3:39])[C:11]([C:9]1[N:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:6]2[N:7]=[C:2]([Cl:1])[N:3]=[CH:4][C:5]=2[CH:10]=1)=[O:13]

Komponenten

7

Edukt 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 735546592-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid

Produkt 1

HCID 866373462-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamideAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid (80 mg, 0.30 mmol), BOP (159 mg, 0.36 mmol) and N,N-diisopropylethylamine (0.078 mL, 0.45 mmol) in DMF (3 mL) is added 0.164 mL of 2 N dimethylamine in THF solution at room temperature. The mixture is stirred at room temperature for 3 h, quenched with 1N NaOH aqueous solution, and extracted with EtOAc. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified by column chromatography (SiO2, 5% MeOH in CH2Cl2) to give 64 mg of 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide.

Aufarbeitung

  1. customquenched with 1N NaOH aqueous solution
  2. extractionextracted with EtOAc
  3. washThe organic extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by column chromatography (SiO2, 5% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-e5c17bd07e9844ec96dde42f1cab072d
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324225B2

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