Triethylamine → Ethyl 4-chloro-6-(2,3-xylidino)-2-pyrimidinylaminoacetate

HRID 637932Notes

Reaction equation

HRID 637932 reaction equation
[H-].[Na+].[NH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl.C(N(CC)CC)C.Cl[C:19]1[N:24]=[C:23]([Cl:25])[CH:22]=[C:21]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[C:28]=2[CH3:34])[N:20]=1>COCCOC.O>[Cl:25][C:23]1[CH:22]=[C:21]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[C:28]=2[CH3:34])[N:20]=[C:19]([NH:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:24]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 24758Sodium hydrideHCID 2723640Glycine ethyl ester, hydrochlorideHCID 134137552,6-Dichloro-N-(2,3-dimethylphenyl)pyrimidin-4-amine

Product 1

HCID 13413749Ethyl 4-chloro-6-(2,3-xylidino)-2-pyrimidinylaminoacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspensione of 100% sodium hydride (27 mg) in anhydrous 1,2-dimethoxyethane (1.5 ml) is treated with small amounts of NH2CH2CO2C2H5.HCl (156 mg). Triethylamine (0.16 ml) and 2,4-dichloro-6-(2,3-xylidino)-pyrimidine (300 mg) are added, and the mixture is refluxed for 18 hours. Triethylamine (0.16 ml) is added again, heating under reflux for 24 hours more. Finally, after cooling, the reaction mixture is diluted with water and extracted with methylene chloride. The organic phase is washed to neutrality and dried over Na2SO4. By evaporation of the solvent and crystallization from ethyl acetate 300 mg of ethyl ester of N-[4-chloro-6-(2,3xylidino)-2-pyrimidinyl]-aminoacetic acid (I, 2) are obtained.

Workup

  1. temperaturethe mixture is refluxed for 18 hours
  2. temperatureheating
  3. temperatureunder reflux for 24 hours more
  4. temperatureFinally, after cooling
  5. extractionextracted with methylene chloride
  6. washThe organic phase is washed to neutrality
  7. dry with materialdried over Na2SO4
  8. customBy evaporation of the solvent and crystallization from ethyl acetate 300 mg of ethyl ester of N-[4-chloro-6-(2,3xylidino)-2-pyrimidinyl]-aminoacetic acid (I, 2)
  9. customare obtained

Sources & evidence

ORD record
ord-e7fa98b85586459ea70a39dcef83c659
Source dataset
uspto-grants-1985_12
Patent number
US04559345

Reaction notes

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