Sulfuric Acid → HCID 22114872, compound

HRID 1276055Notes

Reaction equation

HRID 1276055 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]=[C:9]2[NH:19][CH2:20][CH:21](OC)OC)=[C:4]([F:26])[CH:3]=1.S(=O)(=O)(O)O.[OH-].[Na+]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]3[CH:21]=[CH:20][N:19]=[C:9]23)=[C:4]([F:26])[CH:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 22114886HCID 22114886, compound

Product 1

HCID 22114872HCID 22114872, compound

Procedure

3-(4-Bromo-2-fluorophenyl)-3,4-dihydro-2-((2,2-dimethoxyethyl)amino)-6-trifluoromethylpyrimidin-4-one synthesized in Example 14 was dissolved into concentrated sulfuric acid (100 ml) under ice-cooled condition and stirred for 4 hours at room temperature. The reaction solution was poured into ice water (500 ml), neutralized with an aqueous sodium hydroxide solution under ice-cooled condition, extracted with ethyl acetate and dried on anhydrous magnesium sulfate after washing with water. The solvent was distilled off under reduced pressure and then the thus obtained solid was washed with isopropyl ether to give the compound of interest (17.5 g) as a pale yellow solid.

Workup

  1. temperaturecooled condition
  2. temperaturecooled condition
  3. extractionextracted with ethyl acetate
  4. dry with materialdried on anhydrous magnesium sulfate
  5. washafter washing with water
  6. distillationThe solvent was distilled off under reduced pressure
  7. washthe thus obtained solid was washed with isopropyl ether
  8. customto give the compound of interest (17.5 g) as a pale yellow solid

Sources & evidence

ORD record
ord-24d2d7bf96c14a259abbe4c008257058
Source dataset
uspto-grants-2000_12
Patent number
US06165942

Reaction notes

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