Triethylamine → HCID 178473408, compound

HRID 1789576Notes

Reaction equation

HRID 1789576 reaction equation
[C:1]([N:3]=[C:4]1[NH:9][C:8]([CH3:10])=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[Cl:22])[NH:5]1)#[N:2].C(N(CC)CC)C.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32]>CN(C)C=O.O1CCCC1>[C:1]([N:3]=[C:4]1[NH:9][C:8]([CH3:10])=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[Cl:22])[N:5]1[C:31]([O:33][CH2:34][CH3:35])=[O:32])#[N:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformate2×HCID 178498432HCID 178498432, compound

Product 1

HCID 178473408HCID 178473408, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 2-(cyanoimino)-6-(2,3-dichlorophenyl)-3,6-dihydro-4-methyl-5-pyrimidinecarboxylic acid, methyl ester (444 mg, 1.31 mmoles) in dry dimethylformamide (2 ml) and tetrahydrofuran (2 ml) was cooled to 0° C. and was treated with triethylamine (0.5 ml) followed by ethyl chloroformate (284 mg, 2.62 mmoles). After the addition of ethyl chloroformate, the reaction turned yellow. The cooling bath was removed and stirring was continued at room temperature for 3 hours. The reaction was then diluted with ethyl acetate and washed with water, 5% citric acid, sodium bicarbonate and brine. After drying over magnesium sulfate, the solvent was evaporated and the residue was purified by flash chromatography (12% ethyl acetate in dichloromethane). The resulting product was crystallized from dichloromethane-isopropyl ether to provide 317 mg of the title compound as a colorless solid, melting point 176°-178° C.

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction was then diluted with ethyl acetate
  3. washwashed with water, 5% citric acid, sodium bicarbonate and brine
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent was evaporated
  6. customthe residue was purified by flash chromatography (12% ethyl acetate in dichloromethane)
  7. customThe resulting product was crystallized from dichloromethane-isopropyl ether

Sources & evidence

ORD record
ord-77f9d01c15454a0998d8a1279a36088d
Source dataset
uspto-grants-1987_08
Patent number
US04689414

Reaction notes

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