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

HRID 2093779Notes

Reaction equation

HRID 2093779 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) was heated at 40° C. for 24 h. The solvent was removed in vacuo. The resulting residue was partitioned between EtOAc (350 mL) and water (100 mL). The EtOAc layer was washed with water (3×), saturated aqueous NaCl (1×) and dried over Na2SO4. The resulting EtOAc solution was 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 was removed in vacuo
  2. customThe resulting residue was partitioned between EtOAc (350 mL) and water (100 mL)
  3. washThe EtOAc layer was washed with water (3×), saturated aqueous NaCl (1×)
  4. dry with materialdried over Na2SO4
  5. concentrationThe resulting EtOAc solution was concentrated in vacuo

Sources & evidence

ORD record
ord-ce224eb17d804beeb503e343c7b5eb75
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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