Guanidine Hydrochloride → 2,4-Diaminopyrido[2,3-d]pyrimidine-6-carbonitrile

HRID 4448

Reaktionsgleichung

Reaktionsgleichung von HRID 4448
[NH2:1][C:2]([NH2:4])=[NH:3].Cl.C[O-].[Na+].N[C:10]1[C:15]([C:16]#[N:17])=[CH:14][C:13]([C:18]#[N:19])=[CH:12][N:11]=1.C1CCCCC1.CCOC(C)=O>CCO>[NH2:3][C:2]1[N:4]=[C:16]([NH2:17])[C:15]2[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[N:11][C:10]=2[N:1]=1

Komponenten

6

Edukt 4

HCID 5742Guanidine HydrochlorideHCID 2959122-Aminopyridine-3,5-dicarbonitrileHCID 10942334Sodium MethoxideHCID 21867204Cyclohexane ethylacetate

Produkt 1

HCID 3013972,4-Diaminopyrido[2,3-d]pyrimidine-6-carbonitrileAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Guanidine·HCl (2.66 g, 27.8 mmol) was added to a solution of NaOMe (sodium methoxide) (1.50 g, 27.8 mmol) in absolute EtOH (180 mL). The mixture was stirred at 20°-23° C. for 15 minutes before 5 (2.00 g, 13.9 mmol) was added. After a 24-hour reflux period with rapid stirring, TLC (cyclohexane-EtOAc, 1:1) showed absence of 5. The solid filtered from the cooled mixture was washed on the funnel with H2O and EtOH; yield 95% (2.45 g). A sample of this material (1.0 g) was stirred with near-boiling Me2SO (dimethyl sulfoxide) (250 mL), and the slightly cloudy solution was filtered (Celite) to give a clear, pale-yellow filtrate which was then concentrated by evaporation in vacuo (to about 60 mL). Addition of EtOH (200 mL) gave 7 as a light yellow solid (880 mg); 1H NMR (Me2SO-d6) δ6.97 (2, NH2), 7.84 (s, NH2), 8.87 and 8.91 (two d, 5-H and 7-H, J=2 Hz).

Aufarbeitung

  1. additionwas added
  2. filtrationThe solid filtered from the cooled mixture
  3. washwas washed on the funnel with H2O and EtOH
  4. filtrationthe slightly cloudy solution was filtered (Celite)
  5. customto give a clear, pale-yellow filtrate which
  6. concentrationwas then concentrated by evaporation in vacuo (to about 60 mL)
  7. additionAddition of EtOH (200 mL)

Quellen und Nachweise

ORD-Eintrag
ord-01537abe3d964860950784242d6215b3
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725687

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