Potassium Carbonate → 1-[(2,6-Dimethyl-pyrimidin-4-yl)-amino]4-(4-pyridyl-methyl)-phthalazine

HRID 2054193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2054193
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[N:3]=1.I[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH2:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[N:13][N:12]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:9][C:4]1[N:3]=[C:2]([NH:1][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:13][N:12]=2)[CH:7]=[C:6]([CH3:8])[N:5]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 680392,6-Dimethyl-4-aminopyrimidineHCID 223864621-Iodo-4-(4-pyridyl-methyl)-phthalazine

Produkt 1

HCID 223864801-[(2,6-Dimethyl-pyrimidin-4-yl)-amino]4-(4-pyridyl-methyl)-phthalazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a suspension of 308 mg (2.5 mMol) of 4-amino-2,6-dimethyl-pyrimidine and 694 mg (2.0 mMol) of 1-iodo-4-(4-pyridyl-methyl)-phthalazine in 20 ml of toluene, 415 mg (3.0 mMol) of K2CO3 and 231 mg (0.20 mMol) of tetrakis-(triphenylphosphin)-palladium are added, and the mixture is stirred during 1 h at RT and then 17 h at 110° C. The hot reaction mixture is filtrated, the remaining solid washed out with toluene and petrol ether and discarded. From the filtrate, product crystallizes after cooling. Filtration, washing with toluene/petrol ether and recrystallization from boiling dioxane yields the title compound: m.p 232-233° C.; An. calc.(C20H18N6.0.10 H2O) C, 69.79%; H, 5.33%; N, 24.42%; H2O, 0.52%; An. meas. C, 69.78%; H, 5.32%; N, 24.20%; H2O, 0.5%; FAB-MS (M+H)+=343.

Aufarbeitung

  1. additionare added
  2. custom17 h
  3. customat 110° C
  4. filtrationThe hot reaction mixture is filtrated
  5. washthe remaining solid washed out with toluene and petrol ether
  6. customFrom the filtrate, product crystallizes
  7. temperatureafter cooling
  8. filtrationFiltration
  9. washwashing with toluene/petrol ether and recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-b55f2097f80446559988548195eb3982
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07329660B2

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