Potassium Carbonate → HCID 57955596, compound

HRID 914155Notes

Reaction equation

HRID 914155 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:18][CH2:19][C:20]([F:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][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:18]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:19][C:20]([F:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[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 57955635Ethyl 3-(cyclohexylamino)-2-fluoro-2-methylpropanoate

Product 1

HCID 57955596HCID 57955596, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 2,4-dichloro-5-nitropyrimidine (970 mg, 5 mmol) in anhydrous acetone (20 ml) at 0° C., was added dropwise a solution of ethyl 3-(cyclohexylamino)-2-fluoro-2-methylpropanoate (1.1 g, 4.76 mmol) in acetone (5 mL) over 10 min. After which, potassium carbonate (1.66 g, 12 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 (1.9 g) which was used directly for next step. [M+H] calc'd for C16H22ClFN4O4, 389. found 389.

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

Sources & evidence

ORD record
ord-c0bae99be7ff46358ac573db534ae86a
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

Loading…