Phenethylamine → 4-(N-benzylmethylamino)-2-methyl-6-oxo-7-phenyl-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidine

HRID 1728552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1728552
[NH:1]([C:8]1[C:13]([CH2:14][C:15]([O:17]C)=O)=[C:12](Cl)[N:11]=[C:10]([CH3:20])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([CH2:28][NH2:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:21]([CH2:28][NH:29][C:12]1[C:13]2[CH2:14][C:15](=[O:17])[N:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:8]=2[N:9]=[C:10]([CH3:20])[N:11]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

3

Edukt 2

HCID 1001PhenethylamineHCID 86747976HCID 86747976, Verbindung

Produkt 1

HCID 190143314-(N-benzylmethylamino)-2-methyl-6-oxo-7-phenyl-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidineAusbeute 44,6 %

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 4-anilino-6-chloro-2-methylpyrimidine-5-acetic acid, methyl ester (5.0g, 17.2mM) and benzylmethylamine (2.22ml, 17.2mM) was heated at 160° C. for 3.5 hours. The mixture was cooled and then partitioned between methylene chloride (50ml) and 2M hydrochloric acid (50ml). The organic layer was separated, washed with a solution of sodium hydroxide (2M, 50ml), water, dried and the solvent evaporated. The residue was purified by flash column chromatography on silica (Merck 9385), eluting with ethyl acetate/hexane (20:80, v/v) to give 4-(N-benzylmethylamino)-2-methyl-6-oxo-7-phenyl-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidine (2.64g, 44.6%) m.p. 81°-84° C.; microanalysis, found; C, 73.0; H, 6.0; N, 16.3%; C21H20H40 requires C, 73.3; H, 5.8; N, 16.3%; NMR: DMSOd6 : 2.3(3H, s, pyrimidine-CH3), 3.2(3H,s,N-CH3), 3.95(2H,s,COCH2), 4.85(2H,s,N-CH2), 7.2-7.55(10H, complex, aromatic).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. custompartitioned between methylene chloride (50ml) and 2M hydrochloric acid (50ml)
  3. customThe organic layer was separated
  4. washwashed with a solution of sodium hydroxide (2M, 50ml), water
  5. customdried
  6. customthe solvent evaporated
  7. customThe residue was purified by flash column chromatography on silica (Merck 9385)
  8. washeluting with ethyl acetate/hexane (20:80

Quellen und Nachweise

ORD-Eintrag
ord-914c25346ab64951a8a16fc36e8d38ab
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05328910

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