Water → HCID 22407596, compound

HRID 1756006Notes

Reaction equation

HRID 1756006 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.Cl[C:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH2:20][CH3:21])[N:12]=[CH:11][N:10]=1.[CH2:22](N)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH2:31]>C1(C)C=CC=CC=1>[O:31]1[CH2:21][CH2:20][CH2:13][CH2:14][CH:15]1[O:16][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:7][CH2:6][NH:3][C:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH2:20][CH3:21])[N:12]=[CH:11][N:10]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1001PhenethylamineHCID 8471TriethylamineHCID 183578244-Chloro-5-ethoxycarbonyl-6-ethylpyrimidine

Product 1

HCID 22407596HCID 22407596, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylamine (2.26 g, 22.33 mmol) was added to a solution of ethyl 4-chloro-6-ethylpyrimidine-5-carboxylate (2.41 g, 11.23 mmol) in toluene (10 ml). The mixture was stirred at room temperature. Then, 4-(2-tetrahydropyran-2-yloxy)ethyl)phenethylamine (2.80 g, 11.23 mmol) was added. After stirring for 16 hours, water (40 ml) was added to the reaction mixture. The mixture was extracted with methylene chloride and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=8/2) to give the desired ethyl 4-(2-(4-(2-(tetrahydropyran-2-yloxy)ethyl)phenyl)ethylamino)-6-ethylpyrimidine-5-carboxylate (4.20 g, 87%).

Workup

  1. stirringAfter stirring for 16 hours
  2. extractionThe mixture was extracted with methylene chloride
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=8/2)

Sources & evidence

ORD record
ord-8191814cf12e499caeef919faa9e9259
Source dataset
uspto-grants-1995_08
Patent number
US05439911

Reaction notes

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