Citric Acid → HCID 178493585, compound

HRID 1429178Notes

Reaction equation

HRID 1429178 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[N:3]=1.C1N2CCN(CC2)C1.C(=O)([O-])[O-:21].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[CH3:11][O:10][C:4]1[N:3]=[C:2]([OH:21])[CH:7]=[C:6]([O:8][CH3:9])[N:5]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 9237DabcoHCID 11430Potassium CarbonateHCID 806004-Chloro-2,6-dimethoxypyrimidine

Product 1

HCID 178493585HCID 178493585, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 4-chloro-2,6-dimethoxy-pyrimidine (4.9 g, 28 mmol), DABCO (6.4 g, 57 mmol) and potassium carbonate (13.8 g, 100 mmol) was refluxed in water (150 ml) for one hour. The mixture was cooled acidified with 5% citric acid and extracted three times with ethyl acetate and three times with DCM with about 105 THF and 10% MeOH. The combined organic phases were dried and evaporated which gave the title compound (1.5 g, 34%), (M+H)+1 157.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted three times with ethyl acetate and three times with DCM with about 105 THF and 10% MeOH
  3. customThe combined organic phases were dried
  4. customevaporated which

Sources & evidence

ORD record
ord-d6bed3b2bfe94e3ca2d89ac0f0149c68
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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