2-(3-Chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine → 2-(3-Chloroanilino)-4-(imidazol-5-yl)pyrimidine

HRID 1064306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064306
[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[NH:5][C:6]1[N:11]=[C:10]([C:12]2[N:13]=[CH:14][N:15](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:16]=2)[CH:9]=[CH:8][N:7]=1>CO.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[NH:5][C:6]1[N:11]=[C:10]([C:12]2[NH:13][CH:14]=[N:15][CH:16]=2)[CH:9]=[CH:8][N:7]=1

Komponenten

4

Edukt 1

HCID 222735042-(3-Chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine

Produkt 1

HCID 222734742-(3-Chloroanilino)-4-(imidazol-5-yl)pyrimidineAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(3-chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine (Method 2; 256 mg, 0.5 mmol) in MeOH (3 ml) and 2M hydrochloric acid (1 ml) was stirred for 15 minutes. The volatiles were removed by evaporation and the residue partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, dried and the solvent removed by evaporation. The residue was purified by column chromatography eluting with DCM and 7M methanolic ammonia solution (99.5:0.5 increasing in polarity to 93:7) to give the title compound 102 mg, (75%) as a solid. NMR: 6.95 (dd, 1H), 7.25-7.33 (m, 2H), 7.73 (dd, 1H), 7.81 (d, 2H), 8.06 (s, 1H), 8.46 (d, 1H), 9.68 (s, 1H), 12.48 (br s, 1H); m/z: 270.

Aufarbeitung

  1. customThe volatiles were removed by evaporation
  2. customthe residue partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution
  3. customThe organic layer was separated
  4. customdried
  5. customthe solvent removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with DCM and 7M methanolic ammonia solution (99.5:0.5 increasing in polarity to 93:7)

Quellen und Nachweise

ORD-Eintrag
ord-c4eda35d17aa414391e683ecee4a8562
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06969714B2

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