Pyrimidine → Methyl 3-[cyclopentyl(2-chloro-5-nitropyrimidin-4-yl)amino]propanoate

HRID 2279995Notes

Reaction equation

HRID 2279995 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([O-])([O-])=O.[K+].[K+].[Cl:19][C:20]1[N:25]=[C:24](Cl)[C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1.N1C=CC=NC=1>CC(C)=O>[CH:1]1([N:6]([C:22]2[C:23]([N+:27]([O-:29])=[O:28])=[CH:24][N:25]=[C:20]([Cl:19])[N:21]=2)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 9260PyrimidineHCID 11430Potassium CarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 28307099Methyl 3-(cyclopentylamino)propanoate

Product 1

HCID 57940528Methyl 3-[cyclopentyl(2-chloro-5-nitropyrimidin-4-yl)amino]propanoateYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 3-(cyclopentylamino)propanoate (0.838 g, 0.005 mol, 1 eq) and K2CO3 (0.676 g, 0.005 mol, 1 eq) were added to acetone (5 mL) and the resulting mixture cooled to 0° C. before the dropwise addition of 2,4-dichloro-5-nitropyrimidine (1.04 g, 0.0055 mol, 1.1 eq). The reaction mixture (RM) was warmed to rt and stirring continued for an additional 16h before the addition of a further 0.12 eq of the pyrimidine. Stirring continued for a further 3h. The RM was evaporated under reduced pressure and the product extracted using EtOAc/H2O. The organic extracts were washed with sat NaCl, dried (MgSO4) and evaporated under reduced pressure to give the product as a brown oily residue (1.04 g, 65%); MS+ve: 329.2; Rt=3.78 min (Analytical—1).

Workup

  1. stirringStirring
  2. customThe RM was evaporated under reduced pressure
  3. extractionthe product extracted
  4. washThe organic extracts were washed with sat NaCl
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-37375729f9554534a9447907267db180
Source dataset
uspto-grants-2015_09
Patent number
US09133199B2

Reaction notes

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