Triethylamine → HCID 21473497, compound

HRID 2294129Notes

Reaction equation

HRID 2294129 reaction equation
O[C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[CH:4][N:3]=1.[ClH:11].[CH3:12][NH:13][CH3:14].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C=O)C.S(Cl)(Cl)=O.C(Cl)Cl.O>[Cl:11][C:2]1[C:7]([C:8]([N:13]([CH3:14])[CH3:12])=[O:10])=[CH:6][N:5]=[CH:4][N:3]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 516892Sodium BicarbonateHCID 178524764HCID 178524764, compound

Product 1

HCID 21473497HCID 21473497, compoundYield 57.1%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-hydroxy-5-pyrimidinecarboxylic acid (0.88 g, 6.3 mmol) in 5 drops of DMF and 6 mL of thionyl chloride was heated at reflux for 3 hours. The mixture was concentrated and the residue was dissolved in methylene chloride. A mixture of the residue, dimethylamine hydrochloride (0.62 g, 7.6 mmol) and triethylamine (4.5 mL, 31.5 mmol) in 50 mL of methylene chloride was stirred at 0° C. for 0.5 hours. The mixture was poured into water and aqueous sodium bicarbonate. The mixture was extracted with methylene chloride (2×30 mL) and the extract was washed with brine, dried (Na2SO4) and concentrated by rotary evaporation to give 4-chloro-N,N-dimethyl-5-pyrimidinecarboxamide (0.66 g, 3.6 mmol) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe mixture was concentrated
  4. dissolutionthe residue was dissolved in methylene chloride
  5. extractionThe mixture was extracted with methylene chloride (2×30 mL)
  6. washthe extract was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-e032a3fcc03447c9a8e4fd060d9b3a77
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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