Potassium Carbonate → HCID 86623421, compound

HRID 220720Notes

Reaction equation

HRID 220720 reaction equation
[CH:1]1([NH:6][CH2:7][C:8]([F:14])([F:13])[C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[Cl:21][C:22]1[N:27]=[C:26](Cl)[C:25]([N+:29]([O-:31])=[O:30])=[CH:24][N:23]=1>CC(C)=O.CCOC(C)=O>[Cl:21][C:22]1[N:27]=[C:26]([N:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH2:7][C:8]([F:13])([F:14])[C:9]([O:11][CH3:12])=[O:10])[C:25]([N+:29]([O-:31])=[O:30])=[CH:24][N:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 67117821Methyl 3-(cyclopentylamino)-2,2-difluoropropanoate

Product 1

HCID 86623421HCID 86623421, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Compound methyl 3-(cyclopentylamino)-2,2-difluoropropanoate (400 mg, 2 mmol) was solubilized in acetone (20 mL, dry). The solution was cooled in an ice water bath under a nitrogen atmosphere and K2CO3 (552 mg, 4 mmol) added. To this, a solution of 2,4-dichloro-5-nitropyrimidine (407 mg, 2.1 mmol) in acetone (5 mL, dry) was added dropwise. The reaction mixture was warmed up to room temperature and stirred for 4 hr. After that, it was diluted with EtOAc and washed by brine and water. The organic extracts were dried over MgSO4, filtered and concentrated to yield methyl 3-((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)-2,2-difluoropropanoate which was used directly for next step without further purification. [M+H] calc'd for C13H15ClF2N4O4, 365; found 365.

Workup

  1. temperatureThe solution was cooled in an ice water bath under a nitrogen atmosphere
  2. washwashed by brine and water
  3. dry with materialThe organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f8cb809d19b4ceb86e5b5aa5a65fa9b
Source dataset
uspto-grants-2012_06
Patent number
US08202990B2

Reaction notes

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