Hydroxyacetone → HCID 17979067, compound

HRID 1354156Notes

Reaction equation

HRID 1354156 reaction equation
[OH:1][CH2:2][C:3](=[O:5])[CH3:4].[CH3:6][Li].[Cl:8][C:9]1[CH:14]=[C:13](Cl)[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:8][C:9]1[CH:14]=[C:13]([O:1][CH2:2][C:3]([OH:5])([CH3:6])[CH3:4])[N:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 8299HydroxyacetoneHCID 25517Ammonium ChlorideHCID 709434,6-DichloropyrimidineHCID 178418348HCID 178418348, compound

Product 1

HCID 17979067HCID 17979067, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 20 ml of tetrahydrofuran was dissolved 1 g of 1-hydroxy-2-propanone, to which 26 ml of a 1.14 mol/l solution (diethyl ether solution) of methyl lithium was added dropwise at −78° C. The mixture was stirred at the same temperature for 1 hour. After gradually increasing the temperature up to 0° C., 4 ml of a solution containing 2 g of 4,6-dichloropyrimidine in tetrahydrofuran was added dropwise, followed by further stirring 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.66 g of 4-chloro-6-(2-hydroxy-2-methylpropyloxy)pyrimidine.

Workup

  1. additionwas added dropwise
  2. stirringby further stirring 2 hours
  3. extractionwas extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-201bce8d8108484293098c92b4a34c19
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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