Potassium Carbonate → methyl 3-(N-cyclopentyl-N-(2-methyl-5-nitropyrimidin-4-yl)amino)propionate

HRID 910653Notes

Reaction equation

HRID 910653 reaction equation
[CH:1]1([NH:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:13](=O)([O-])[O-].[K+].[K+].Cl[C:20]1[N:25]=[C:24](Cl)[C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1>CC(C)=O>[CH:1]1([N:6]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:22]2[C:23]([N+:27]([O-:29])=[O:28])=[CH:24][N:25]=[C:20]([CH3:13])[N:21]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 28307099Methyl 3-(cyclopentylamino)propanoate

Product 1

HCID 67393001methyl 3-(N-cyclopentyl-N-(2-methyl-5-nitropyrimidin-4-yl)amino)propionateYield 69.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Methyl 3-(cyclopentylamino)propanoate (1.78 g, 10.4 m mole) and potassium carbonate (1.52 g, 11.0 m mol) in acetone (25 ml) was stirred at 0° C. during the addition of a solution of 2,4-dichloro-5-nitropyrimidine (2.04 g, 10.4 m mol) in acetone (15 ml). The mixture was stirred at ambient temperature overnight, concentrated and diluted with ethyl acetate/water. The mixture was extracted ×3 with ethyl acetate, dried over magnesium sulphate and concentrated to an amber oil which solidified on standing. Flash chromatography on silica gel eluting with 30% ethyl acetate/petrol gave methyl 3-(N-cyclopentyl-N-(2-methyl-5-nitropyrimidin-4-yl)amino)propionate as a pale yellow solid (2.24 g, 65%). NMR CDCl3 1.50-2.07 (8H, m), 2.70-2.82 (2H, m), 3.65-3.90 (6H, m), 8.72 (1H, s).

Workup

  1. concentrationconcentrated
  2. additiondiluted with ethyl acetate/water
  3. extractionThe mixture was extracted ×3 with ethyl acetate
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to an amber oil which

Sources & evidence

ORD record
ord-5ba52b5a97dd4e19b505a7f5bd16bcbe
Source dataset
uspto-grants-2011_09
Patent number
US08022202B2

Reaction notes

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