Guanidine Hydrochloride → 2,4-diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidine

HRID 34462

Reaktionsgleichung

Reaktionsgleichung von HRID 34462
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH2:13][C:14](=[CH:17]N2CCOCC2)[C:15]#[N:16])[C:6]2[CH:7]=[CH:8][CH2:9][O:10][C:5]=2[C:4]=1[O:24][CH3:25].Cl.NC1C=CC=CC=1.Cl.[NH2:35][C:36]([NH2:38])=[NH:37].C[O-].[Na+]>>[NH2:37][C:36]1[N:38]=[C:15]([NH2:16])[C:14]([CH2:13][C:11]2[C:6]3[CH:7]=[CH:8][CH2:9][O:10][C:5]=3[C:4]([O:24][CH3:25])=[C:3]([O:2][CH3:1])[CH:12]=2)=[CH:17][N:35]=1

Komponenten

5

Edukt 4

HCID 5742Guanidine HydrochlorideHCID 8870Benzenamine hydrochloride (1:1)HCID 10942334Sodium MethoxideHCID 542807632-(7,8-Dimethoxy-2H-1-benzopyran-5-ylmethyl)-3-morpholino acrylonitrile

Produkt 1

HCID 128497722,4-diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidineAusbeute 42,7 %

Versuchsvorschrift

2-(7,8-Dimethoxy-2H-1-benzopyran-5-ylmethyl)-3-morpholino acrylonitrile (562 g, 1.64 mol) and aniline hydrochloride (234 g, 1.80 mol) were refluxed in SD3A (2.4 L) for one hour. The reaction was cooled, and guanidine hydrochloride (313 g, 3.28 mol) and sodium methoxide (275 g, 5.08 mol) were added. After continued reflux, the product crystallized from the cooled reaction mixture. Filtration followed by water wash (2 L) gave 2,4-diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidine (220 g, 42.7%). Crystallization from ethanol-water gave title compound, mp 235°-238°, identical to the product of Example 1C.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. temperatureAfter continued reflux
  3. customthe product crystallized from the cooled reaction mixture
  4. filtrationFiltration
  5. washwash (2 L)

Quellen und Nachweise

ORD-Eintrag
ord-cee52d64b5dc4625a65ee23e86a5187e
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761475

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