Methyl iodide → 7-Methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine

HRID 1111734

Reaktionsgleichung

Reaktionsgleichung von HRID 1111734
[C:1]1([NH2:15])[N:2]=[C:3]([NH2:14])[N:4]=[C:5]2[C:10]=1[C:9]1[CH:11]=[CH:12][NH:13][C:8]=1[CH:7]=[CH:6]2.[H-].[Na+].CI.[C:20](=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.CN(C)C=O>[CH3:20][N:13]1[C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[C:1]([NH2:15])[N:2]=[C:3]([NH2:14])[N:4]=3)[C:9]=2[CH:11]=[CH:12]1

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 178508668HCID 178508668, Verbindung

Produkt 1

HCID 4678897-Methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 5.98 g. 7H-pyrrolo[3,2-f]quinazoline-1,3-diamine in 200 ml. dry dimethylformamide is stirred under nitrogen and 1.58 g. ca. 50% sodium hydride-mineral oil dispersion is added carefully. After stirring for one hour, a solution of 4.47 g. (2.0 ml.) methyl iodide in 10 ml. dry dimethylformamide is added and stirring is continued. Two hours later, 15 ml. gl. acetic acid are added and the reaction mixture is freed of solvent (in vacuo). The residue is stirred with excess aqueous potassium carbonate solution for several hours and the solids are collected, washed with water and dried. A solution of this crude product in 200 ml. water-10 ml. gl. acetic acid is washed with ether. Basification of the acidic solution gives a precipitate that is washed with water and then is crystallized from methanol-acetone to yield 3.44 g. title compound as a hydrate bearing one-third molecule of water per molecule of diamine, m.p. 250°; NMR (dDMSO): δ 3.88 (singlet, 7-CH3), 7.02 (doublet, J=3Hz, 9H), 7.15 (doublet, J=9Hz, 5 or 6H), 7.41 (doublet, J=3Hz, 8H), 7.72 (doublet, J=9Hz, 5 or 6H) p.p.m.; λmax95%EtOH 234 (ε 25,280), 258 (ε 24,540), 317 (ε 9,090), 345 sh (ε 7,810) nm; λmin95%EtOH 243 (ε 23,570), 280 (ε 2,040)nm.

Aufarbeitung

  1. stirringstirring
  2. customTwo hours
  3. customthe solids are collected
  4. washwashed with water
  5. customdried
  6. washacetic acid is washed with ether
  7. customBasification of the acidic solution gives a precipitate that
  8. washis washed with water
  9. customis crystallized from methanol-acetone
  10. customto yield 3.44 g

Quellen und Nachweise

ORD-Eintrag
ord-63157b9d0ae4403d80368fe929228e3c
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04118561

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