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Pyridine → 2-(isopropylamino)-4-(5-(phenylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

HRID 887367
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 887367
[NH2:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([NH:19][CH:20]([CH3:22])[CH3:21])[N:12]=3)=[CH:9][N:8]([S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:5]2=[N:6][CH:7]=1.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:20]([NH:19][C:13]1[N:12]=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([NH:1][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH:3]=3)[N:8]([S:23]([C:26]3[CH:27]=[CH:28][C:29]([CH3:30])=[CH:31][CH:32]=3)(=[O:24])=[O:25])[CH:9]=2)[C:16]([C:17]#[N:18])=[CH:15][N:14]=1)([CH3:21])[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 686682684-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(isopropylamino)pyrimidine-5-carbonitrile

Produkt 1

HCID 686678792-(isopropylamino)-4-(5-(phenylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrileAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895
Cupric acetate
Katalysator
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(isopropylamino)pyrimidine-5-carbonitrile (0.204 g, 0.455 mmol) in DCM (12 mL) was treated with phenylboronic acid (0.111 g, 0.910 mmol, 2.0 Eq), copper acetate (0.124 g, 0.682 mmol, 1.5 Eq), pyridine (0.074 mL, 0.910 mmol, 2.0 Eq) and 4 Angstrom molecular sieves (0.600 g) and the reaction was allowed to stir at room temperature for 16 hours. The reaction mixture was quenched with 4M Ammonia in MeOH (12 mL) and filtered through a plug of celite whilst washing through with further DCM/MeOH. The combined washes were evaporated to dryness and purified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/Petroleum Ether) to give the title compound as a yellow solid (85 mg, 36%).

Aufarbeitung

  1. customThe reaction mixture was quenched with 4M Ammonia in MeOH (12 mL)
  2. filtrationfiltered through a plug of celite
  3. washwhilst washing through with further DCM/MeOH
  4. customThe combined washes were evaporated to dryness
  5. custompurified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/Petroleum Ether)

Quellen und Nachweise

ORD-Eintrag
ord-8a7812f247ec43d7bfad9949216c4dfb
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08247421B2

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