Triethylamine → 2,5-Dichloro-N-(5-methyl-1H-pyrazol-3-yl)-4-pyrimidinamine

HRID 415424Notes

Reaction equation

HRID 415424 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH2:7])[CH:3]=1.C(N(CC)CC)C.[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([Cl:23])=[CH:18][N:17]=1>CCO>[Cl:15][C:16]1[N:21]=[C:20]([NH:7][C:4]2[CH:3]=[C:2]([CH3:1])[NH:6][N:5]=2)[C:19]([Cl:23])=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 114022722,5-Dichloro-N-(5-methyl-1H-pyrazol-3-yl)-4-pyrimidinamineYield 61.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-methyl-1H-pyrazol-3-amine (2.78 g, 27.3 mmol) in absolute EtOH (30 ml) was added triethylamine (5 ml) and 2,4,5-trichloropyrimidine (5.0 g, 27.3 mmol) and the resulting solution was aged at room temperature for 12 hours. The mixture was partitioned between EtOAc and H2O, the organic layer was washed with brine and dried. The solvents were removed under reduced pressure to give the title compound (4.1 g). m/z: 245.

Workup

  1. customThe mixture was partitioned between EtOAc and H2O
  2. washthe organic layer was washed with brine
  3. customdried
  4. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-c3aa3bf76eee4232a09677f9c802e007
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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