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

HRID 2091926Notes

Reaction equation

HRID 2091926 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH2:7])[CH:3]=1.[Cl:8][C:9]1[N:14]=[C:13](Cl)[C:12]([Cl:16])=[CH:11][N:10]=1.C([O-])([O-])=O.[Na+].[Na+]>CCO>[Cl:8][C:9]1[N:14]=[C:13]([NH:7][C:4]2[CH:3]=[C:2]([CH3:1])[NH:6][N:5]=2)[C:12]([Cl:16])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 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-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 5-methyl-1H-pyrazol-3-amine (3.00 g, 30.9 mmol), 2,4,5-trichloropyrimidine (5.67 g, 30.9 mmol, 1 equiv.) and Na2CO3 (3.60 g, 34.0 mmol, 1.1 equiv.) in EtOH (100 mL) is heated at 40° C. for 24 h. The solvent is removed in vacuo. The resulting residue is partitioned between EtOAc (350 mL) and water (100 mL). The EtOAc layer is washed with water (3×), saturated aqueous NaCl (1×) and dried over Na2SO4. The resulting EtOAc solution is concentrated in vacuo, providing the product 2,5-dichloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine; ESMS m/z 244.0 (M+H+).

Workup

  1. customThe solvent is removed in vacuo
  2. customThe resulting residue is partitioned between EtOAc (350 mL) and water (100 mL)
  3. washThe EtOAc layer is washed with water (3×), saturated aqueous NaCl (1×)
  4. dry with materialdried over Na2SO4
  5. concentrationThe resulting EtOAc solution is concentrated in vacuo

Sources & evidence

ORD record
ord-3493f4555b59420c9c6e6cb4ededc59e
Source dataset
uspto-grants-2013_05
Patent number
US08440681B2

Reaction notes

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