Water → 5-Chloro-6-(2,4-difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

HRID 1851161Notes

Reaction equation

HRID 1851161 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])=[C:6](Cl)[N:5]2[N:17]=[C:18]([CH3:20])[N:19]=[C:4]2[N:3]=1.O.C1COCC1.[NH4+].[Cl-]>C(O)C.[Zn]>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])=[CH:6][N:5]2[N:17]=[C:18]([CH3:20])[N:19]=[C:4]2[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 867030245,7-Dichloro-6-(2,4-difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 867030235-Chloro-6-(2,4-difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidineYield 57%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

2.35 g (7.5 mmol) 5,7-Dichloro-6-(2,4-difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine are given in 189 mL ethanol, 135 mL water and 73 mL THF. 1.89 g (35.3 mmol) NH4Cl and 3.1 g (47.7 mmol) zinc powder are added and the mixture is stirred at room temperature for 3 h. The reaction mixture is filtered and the organic solvents are removed. The residue is diluted with water and extracted three times with ethyl acetate. The combined organic layers are washed with brine and dried over Na2SO4. After evaporation of the solvent, the residue is purified by chromatography. 1.2 g (51.6%) of the desired product are obtained.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe organic solvents are removed
  3. additionThe residue is diluted with water
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter evaporation of the solvent
  8. customthe residue is purified by chromatography

Sources & evidence

ORD record
ord-75d4ab78b469461a97660689e1f5a75f
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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