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

HRID 1897646Notes

Reaction equation

HRID 1897646 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; SMS 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-5e34c8ea4be34bf98d2d31bd96e9fba3
Source dataset
uspto-grants-2013_08
Patent number
US08519129B2

Reaction notes

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