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

HRID 2119311Notes

Reaction equation

HRID 2119311 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 22386462HCID 22386462, compound

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 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.

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 ether and recrystallization

Sources & evidence

ORD record
ord-2943f7e6074142b0afd0560194672694
Source dataset
uspto-grants-2004_02
Patent number
US06686347B2

Reaction notes

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