Dimethylformamide → HCID 12056737, compound

HRID 1862221Notes

Reaction equation

HRID 1862221 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.Br[CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH:10]([C:11]([O:13][CH3:14])=[O:12])[CH3:15])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 145957002-Chloro-5-pyrimidinol

Product 1

HCID 12056737HCID 12056737, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.17 g of 2-chloro-5-hydroxypyrimidine, 0.22 g of methyl 2-bromopropionate, 0.20 g of anhydrous potassium carbonate and 2.6 ml of N,N-dimethylformamide was stirred at 60° C. for 1 hour. The reaction solution was cooled to room temperature, then, poured into water, and extracted with t-butyl methyl ether. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.17 g of 2-chloro-5-[1-(methoxycarbonyl)ethoxy]pyrimidine.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with t-butyl methyl ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8e0f76e6de2741159ce368aab9226af2
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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