Water → 5-(4-Nitrophenyl)thieno[2,3-d]pyrimidine-2,4-diamine

HRID 227631

Reaktionsgleichung

Reaktionsgleichung von HRID 227631
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=O)=[CH:11][CH:10]=2)[C:6]=1[C:7]#[N:8].Cl.Cl[C:20]([NH2:22])=[NH:21].[OH2:23]>COCCOCCOC>[N+:15]([C:12]1[CH:11]=[CH:10][C:9]([C:5]2[C:6]3[C:7]([NH2:8])=[N:21][C:20]([NH2:22])=[N:1][C:2]=3[S:3][CH:4]=2)=[CH:14][CH:13]=1)([O-:17])=[O:23]

Komponenten

5

Edukt 3

HCID 962WaterHCID 3084509Chloroformamidinium chlorideHCID 156061132-Amino-4-(4-nitrophenyl)thiophene-3-carbonitrile

Produkt 1

HCID 690630455-(4-Nitrophenyl)thieno[2,3-d]pyrimidine-2,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Versuchsvorschrift

A suspension of Example 58B (1 g, 4.08 mmol) and chloroformamidine hydrochloride (1.17 g, 10.2 mmol) in diglyme (40 mL) was heated to 130° C. for 15 hours. The mixture was cooled to room temperature, diluted with water, and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The residue was further concentrated under a stream of nitrogen, and purified by silica gel chromatography with 5 to 7% methanol/dichloromethane to provide 0.26 g of the desired product. MS (ESI(+)) m/e 288 (M+H)+.

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationThe residue was further concentrated under a stream of nitrogen
  7. custompurified by silica gel chromatography with 5 to 7% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-f20ae985763d49b29e6997f2e3bf926d
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560552B2

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