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

HRID 34467

Reaktionsgleichung

Reaktionsgleichung von HRID 34467
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].NC(N)=N.[CH3:13][O:14][C:15]1[CH:24]=[C:23]([CH:25]=[C:26]([CH2:29]OC)[C:27]#[N:28])[C:18]2[CH:19]=[CH:20][CH2:21][O:22][C:17]=2[C:16]=1[O:32][CH3:33]>CO>[NH2:4][C:3]1[N:5]=[C:27]([NH2:28])[C:26]([CH2:25][C:23]2[C:18]3[CH:19]=[CH:20][CH2:21][O:22][C:17]=3[C:16]([O:32][CH3:33])=[C:15]([O:14][CH3:13])[CH:24]=2)=[CH:29][N:2]=1

Komponenten

6

Edukt 4

HCID 3520GuanidineHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 543734473-(7,8-Dimethoxy-2H-1-benzopyran-5-yl)-2-methoxymethylpropenenitrile

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
3 °C

Versuchsvorschrift

Guanidine hydrochloride (11.46 g, 0.12 mole) in methanol (25 mL) was added to sodium methoxide (6.55 g, 0.12 mole) in methanol (40 mL) and the resultant sodium chloride was filtered and washed with methanol (10 mL). The guanidine solution was added to 3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)-2-methoxymethylpropenenitrile (11.5 g, 0.04 mole) and the mixture heated at reflux for 2 hr. Cooling the mixture at 3° C. provided 5.38 g of yellow solid in two crops. HPLC assayed yield of 28.6%. A sample recrystallized from alcohol/water gave mp 232°-4° C.

Aufarbeitung

  1. filtrationthe resultant sodium chloride was filtered
  2. washwashed with methanol (10 mL)
  3. temperaturethe mixture heated
  4. temperatureat reflux for 2 hr

Quellen und Nachweise

ORD-Eintrag
ord-817e59b075864a43ba1165743bca3c56
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761475

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