Sodium Carbonate → HCID 59586795, compound

HRID 536328Notes

Reaction equation

HRID 536328 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 was heated at 60° C. overnight. The reaction mixture was concentrated and then partitioned between EtOAc and brine. The collected organic extracts were 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 was concentrated
  2. custompartitioned between EtOAc and brine
  3. dry with materialThe collected organic extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. custompurified with silica gel chromatography (MeOH/DCM: 1/9)

Sources & evidence

ORD record
ord-c26fb2c8dd604758be4030e69ec25308
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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