Hydrochloric Acid → 2,4-Diamino-5-(5-amino-6-methyl-8-quinolylmethyl)pyrimidine dihydrochloride

HRID 280019

Reaktionsgleichung

Reaktionsgleichung von HRID 280019
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.CC1C([N+]([O-])=O)=C2C(=CC=1)N=CC=C2.[NH2:27][C:28]1[N:33]=[C:32]([NH2:34])[C:31]([CH2:35]O)=[CH:30][N:29]=1.[ClH:37]>C(O)(=O)C>[ClH:37].[ClH:37].[NH2:27][C:28]1[N:33]=[C:32]([NH2:34])[C:31]([CH2:35][C:9]2[CH:10]=[C:11]([CH3:12])[C:2]([NH2:1])=[C:3]3[C:8]=2[N:7]=[CH:6][CH:5]=[CH:4]3)=[CH:30][N:29]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 900096-Methyl-5-nitroquinolineHCID 2958782,4-Diamino-5-pyrimidinemethanolHCID 30221825-Amino-6-methylquinoline

Produkt 1

HCID 201297742,4-Diamino-5-(5-amino-6-methyl-8-quinolylmethyl)pyrimidine dihydrochlorideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 5-amino-6-methylquinoline (2.16 g, 13.7 mmol), prepared by reduction of 6-methyl-5-nitroquinoline (R. Long and K. Schofield, J. Chem. Soc. 1953, 2350), 2,4-diamino-5-hydroxymethylpyrimidine (1.91 g, 13.6 mmol), concentrated hydrochloric acid (1.9 mL), and glacial acetic acid was refluxed for 2 hr. The cooled reaction mixture was filtered and the precipitate washed with ether and dried (4.17 g). Recrystallization from aqueous ethanol with hydrochloric acid gave title compound as red-orange solid (2.08 g, 40%); mp >290° dec. Anal. Calcd for C15H16N6.2HCl.2H2O: C, 46.28; H, 5.70; N, 21.59; Cl, 18.21. Found: C, 46.13; H, 5.61; N, 21.66; Cl, 18.25.

Aufarbeitung

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. washthe precipitate washed with ether
  4. customdried (4.17 g)
  5. customRecrystallization from aqueous ethanol with hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-4a91c58276314f8faf2e21f4f1b69ca0
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587342

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