1-Butanol → HCID 86618739, compound

HRID 1747694Notes

Reaction equation

HRID 1747694 reaction equation
[Cl:1][C:2]1[C:7]([N:8]([CH3:17])[C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6](Cl)[N:5]=[CH:4][N:3]=1.C(O)CCC.[OH-].[NH4+:25]>>[NH2:25][C:6]1[C:7]([N:8]([CH3:17])[C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 3

HCID 2631-ButanolHCID 14923Ammonium Hydroxide2×HCID 86618738HCID 86618738, compound

Product 1

HCID 86618739HCID 86618739, compound

Procedure

To a solution of N-(4,6-dichloropyrimidin-5-yl)-N-methylbenzamide (0.455 g, 0.00161 mol) in 1-butanol (5 mL, 0.05 mol) was added ammonium hydroxide (0.50 mL, 0.013 mol) and the mixture was refluxed for 24 h. To the reaction was added ammonium hydroxide (1.0 mL, 0.026 mol) and the mixture was refluxed for 24 h, cooled, extracted with a mixture of ethyl acetate:isopropanol, washed with saturated aqueous sodium bicarbonate, brine, dried (Na2SO4), filtered, concentrated and triturated in diethyl ether to obtain 284 mg (67.1%).

Workup

  1. temperaturethe mixture was refluxed for 24 h
  2. temperaturethe mixture was refluxed for 24 h
  3. temperaturecooled
  4. extractionextracted with a mixture of ethyl acetate
  5. washisopropanol, washed with saturated aqueous sodium bicarbonate, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customtriturated in diethyl ether
  10. customto obtain 284 mg (67.1%)

Sources & evidence

ORD record
ord-f219ea5cfccf4e568ab1a27ff0b26256
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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