Potassium Carbonate → HCID 86623421, compound

HRID 1880989Notes

Reaction equation

HRID 1880989 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 the desired product 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-b48cf5a19a0147e3b0324c65ab7c1fe0
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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