Potassium Carbonate → Ethyl 3-((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)-2-fluoro-2-methylpropanoate

HRID 914145Notes

Reaction equation

HRID 914145 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH:12]1([NH:17][CH2:18][C:19]([F:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([N:17]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:18][C:19]([F:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 57955537Ethyl 3-(cyclopentylamino)-2-fluoro-2-methylpropanoate

Product 1

HCID 57955550Ethyl 3-((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)-2-fluoro-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 2,4-dichloro-5-nitropyrimidine (2.14 g, 11.0 mmol) in anhydrous acetone (30 ml) at 0° C., was added dropwise a solution of compound ethyl 3-(cyclopentylamino)-2-fluoro-2-methylpropanoate (2 g, 9.22 mmol) in acetone (10 mL) over 10 min. After which, potassium carbonate (3.8 g, 27.7 mmol) was added and the whole was stirred at rt for 18 h. After evaporation in vacuo, the residue was partitioned between ethyl acetate (200 ml) and water (200 ml). The organic layer was washed with NaHCO3, brine and water, dried over Na2SO4 and concentrated in vacuo to give a red residue which was used directly for next step. [M+H] calc'd for C15H20ClFN4O4, 375. found 375.

Workup

  1. customAfter evaporation in vacuo
  2. customthe residue was partitioned between ethyl acetate (200 ml) and water (200 ml)
  3. washThe organic layer was washed with NaHCO3, brine and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give a red residue which

Sources & evidence

ORD record
ord-a7b7480bda904b12a26d525c031c3042
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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