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

HRID 1072547Notes

Reaction equation

HRID 1072547 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

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 other and recrystallization from boiling dioxane yields the title compound: m.p 232-233° C.; An. calc.(C20H18N6.0.10H2O): 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.

Workup

  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 other and recrystallization

Sources & evidence

ORD record
ord-ee08f5682e1b48ebacd8e576fdabe403
Source dataset
uspto-grants-2005_06
Patent number
US06911440B2

Reaction notes

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