Sodium Carbonate → HCID 59586795, compound

HRID 2091938Notes

Reaction equation

HRID 2091938 reaction equation
[CH3:1][C:2]1[O: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])[O:6][N:5]=2)[C:12]([Cl:16])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 661723-Amino-5-methylisoxazoleHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 59586795HCID 59586795, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture 5-methylisoxazol-3-amine (98 mg, 1.0 mmol), 2,4,5-trichloropyrimidine (344 μL, 3.0 mmol), and sodium carbonate (106 mg, 1.0 mmol) in 3 mL of EtOH is heated at 60° C. over night. The reaction mixture is concentrated and then partitioned between EtOAc and brine. The collected organic extracts are dried (Na2SO4), concentrated in vacuo, and purified with silica gel chromatography (MeOH/DCM: 1/9) to afford N-(2,5-dichloropyrimidin-4-yl)-5-methylisoxazol-3-amine; ESMS m/z 245.0 (M+H+).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompartitioned between EtOAc and brine
  3. dry with materialThe collected organic extracts are dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. custompurified with silica gel chromatography (MeOH/DCM: 1/9)

Sources & evidence

ORD record
ord-9b337fc6230e454aaa034f3794de7fb2
Source dataset
uspto-grants-2013_05
Patent number
US08440681B2

Reaction notes

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