Water → 5-(2-Amino-pyrimidin-4-yl)-2-(2,4-dichloro-phenyl)-1h-pyrrole-3-carbonitrile

HRID 1948837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948837
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:10][C:11]([C:16](=O)/[CH:17]=[CH:18]/N(C)C)=[CH:12][C:13]=1[C:14]#[N:15].C(=O)(O)O.[NH2:27][C:28]([NH2:30])=[NH:29].O>CN(C)C=O>[NH2:29][C:28]1[N:30]=[C:16]([C:11]2[NH:10][C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[C:13]([C:14]#[N:15])[CH:12]=2)[CH:17]=[CH:18][N:27]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 286947Carbonic acid-guanidine (1:1)2×HCID 462215562-(2,4-Dichloro-phenyl)-5-((e)-3-dimethylamino-acryloyl)-1h-pyrrole-3-carbonitrile

Produkt 1

HCID 442513475-(2-Amino-pyrimidin-4-yl)-2-(2,4-dichloro-phenyl)-1h-pyrrole-3-carbonitrileAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a suspension of 2-(2,4-dichloro-phenyl)-5-((E)-3-dimethylamino-acryloyl)-1H-pyrrole-3-carbonitrile (6.80 g, 20.35 mmol) in 82 mL of N,N-dimethylformamide was added guanidine carbonate (9.17 g, 101.75 mmol). The mixture was heated to 110° C. for 18 hours under efficient stirring. Then, a further amount of guanidine carbonate (1.83 g; 20.35 mmol) was added to the mixture and heating to 115° C. was prolonged for additional 22 hours. The resulting mixture was diluted by dropwise addition of 325 mL of water over 30 minutes. The solid was isolated by filtration, washed with 100 mL of water, dried in the air and, finally, in a vacuum oven at 60° C. affording 5.58 g of product as a light brown powder. Yield=83%.

Aufarbeitung

  1. temperatureheating to 115° C.
  2. customThe solid was isolated by filtration
  3. washwashed with 100 mL of water
  4. customdried in the air

Quellen und Nachweise

ORD-Eintrag
ord-86ad13a40015422799eb249c7800c0e3
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399668B2

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