Sodium Bicarbonate → HCID 58484961, compound

HRID 1255432Notes

Reaction equation

HRID 1255432 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.[F:12][C:13]1([F:27])[CH2:17][CH2:16][C@@H:15]([NH:18][CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])[CH2:14]1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([N:18]([C@@H:15]2[CH2:16][CH2:17][C:13]([F:12])([F:27])[CH2:14]2)[CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 58484952HCID 58484952, compound

Product 1

HCID 58484961HCID 58484961, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,4-Dichloro-5-nitropyrimidine (2.18 g, 11.25 mmol) was added to a mixture of (R)-methyl 3-(3,3-difluorocyclopentylamino)-2,2-dimethylpropanoate (2.65 g, 11.25 mmol) and sodium bicarbonate (3.78 g, 44.98 mmol) in dichloromethane (10 mL) and petroleum ether (40 mL). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane and dried over magnesium sulfate. The solids were filtered off, rinsing with more dichloromethane. The mother liquors were adsorbed on silica gel and concentrated in vacuo. The residue was purified by flash column chromatography to afford the title compound as yellow solid (2.74 g, 62% yield).

Workup

  1. dry with materialdried over magnesium sulfate
  2. filtrationThe solids were filtered off
  3. washrinsing with more dichloromethane
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-704b4a736adc42e09786b64fdcabccb5
Source dataset
uspto-grants-2013_06
Patent number
US08461149B2

Reaction notes

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