2-Amino-5-bromopyrimidine → HCID 86654457, compound

HRID 1187964Notes

Reaction equation

HRID 1187964 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:11]=[C:12]([C:17]2([C:32]([F:35])([F:34])[F:33])[O:21][N:20]=[C:19]([C:22]3[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[C:24]([CH3:31])[CH:23]=3)[CH2:18]2)[CH:13]=[C:14]([Cl:16])[CH:15]=1>N1C=CC=CC=1>[Br:8][C:5]1[CH:4]=[N:3][C:2]([NH:1][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:22]([C:19]3[CH2:18][C:17]([C:12]4[CH:13]=[C:14]([Cl:16])[CH:15]=[C:10]([Cl:9])[CH:11]=4)([C:32]([F:35])([F:34])[F:33])[O:21][N:20]=3)=[CH:23][C:24]=2[CH3:31])=[N:7][CH:6]=1

Participants

4

Reactant 2

HCID 2313102-Amino-5-bromopyrimidineHCID 866114794-(5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride

Product 1

HCID 86654457HCID 86654457, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a solution of 2.87 g of 2-amino-5-bromopyrimidine in 40 mL of pyridine, 6.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl-chloride synthesized in Step 4 of Synthetic Example 1 was added at room temperature with stirring, and stirred at the same temperature for 2 days. The solvent was distilled off under reduced pressure, the residue was dissolved in 30 mL of 1,4-dioxane, a solution of 3.09 g of potassium hydroxide in 30 mL of water was added and stirred at room temperature for 3 hours. After the completion of the reaction, 20 mL of hydrochloric acid was added in the reaction mixture under cooling with ice and with stirring, extracted with ethyl acetate (50 mL×1), the organic phase was washed with 50 mL of 3N hydrochloric acid, and dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with neutral alumina column chromatography that was eluated with chloroform to obtain 5.52 g of the aimed product as white crystal.

Workup

  1. stirringstirred at the same temperature for 2 days
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in 30 mL of 1,4-dioxane
  4. additiona solution of 3.09 g of potassium hydroxide in 30 mL of water was added
  5. stirringstirred at room temperature for 3 hours
  6. customAfter the completion of the reaction, 20 mL of hydrochloric acid
  7. additionwas added in the reaction mixture
  8. temperatureunder cooling with ice
  9. stirringwith stirring
  10. extractionextracted with ethyl acetate (50 mL×1)
  11. washthe organic phase was washed with 50 mL of 3N hydrochloric acid
  12. dry with materialdried over saturated sodium chloride aqueous solution
  13. distillationanhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure
  14. customThe residue was purified with neutral alumina column chromatography that

Sources & evidence

ORD record
ord-1a7dbe5c595f4ee7a59d2b28e0b34777
Source dataset
uspto-grants-2014_03
Patent number
US08673951B2

Reaction notes

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