Hydrochloric Acid → 5-(3,4-Dimethoxy-5-styryl-benzyl)pyrimidine-2,4-diamine

HRID 963390

Reaktionsgleichung

Reaktionsgleichung von HRID 963390
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16](I)[C:17]=1[O:18][CH3:19])[CH2:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1.[CH2:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.Cl>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([CH:21]=[CH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]=1[O:18][CH3:19])[CH2:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7501StyreneHCID 8471TriethylamineHCID 111010945-(3,4-Dimethoxy-5-iodo-benzyl)pyrimidine-2,4-diamine

Produkt 1

HCID 542175855-(3,4-Dimethoxy-5-styryl-benzyl)pyrimidine-2,4-diamineAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 500 mg of 5-(3,4-dimethoxy-5-iodo-benzyl)pyrimidine-2,4-diamine, 1.53 g of styrene, 1.46 g of triethylamine and 31 mg of palladium-(II) acetate in 25 ml of dioxan is held at reflux under argon for 14 hrs. The mixture is poured on to ice-water, adjusted to pH 5 to 7 with 3N aqueous hydrochloric acid and extracted with methylene chloride. The organic phase is dried over magnesium sulphate, concentrated and the residue is chromatographed on silica gel with methylene chloride/methanol 97:3. 252 mg (53%) of 5-(3,4-dimethoxy-5-styryl-benzyl)pyrimidine-2,4-diamine are isolated as an orange solid. M.p.226°.

Aufarbeitung

  1. temperatureat reflux under argon for 14 hrs
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated
  5. customthe residue is chromatographed on silica gel with methylene chloride/methanol 97:3

Quellen und Nachweise

ORD-Eintrag
ord-3f97be4ee11d4e57b9cc1dd1d49000af
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763450

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