2,4-Dichloropyrimidine → 2-Chloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine

HRID 2105228Notes

Reaction equation

HRID 2105228 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:14]=[C:13]([CH3:15])[NH:12][N:11]=1.C(N(CC)C(C)C)(C)C>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:9][C:10]2[CH:14]=[C:13]([CH3:15])[NH:12][N:11]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-

Product 1

HCID 231324822-Chloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amineYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2,4-dichloropyrimidine (2.97 g, 20 mmol), 3-amino-5-methyl-1H-pyrazole (2.14 g, 22 mmol), and N,N-diisopropylethylamine (2.82 g, 22 mmol) in dry THF (75 ml) was stirred at 50° C. for 18 hours. The solvent was removed by evaporation, and the residue partitioned between DCM (75 ml) and water (50 ml). The resulting precipitate was collected by filtration washed with water and then ether, and dried under vacuum at 50° C. to give the title compound (1.08 g, 26%) as a colourless crystalline solid.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue partitioned between DCM (75 ml) and water (50 ml)
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. dry with materialether, and dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-a283c362b01d4af99c6c03a24b960f4f
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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