Potassium Carbonate → HCID 86617583, compound

HRID 2234414Notes

Reaction equation

HRID 2234414 reaction equation
[CH:1]1([NH:6][CH:7]([CH3:13])[CH2:8][C:9]([NH:11][CH3:12])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:14][C:15]1[C:16](Cl)=[N:17][C:18]([Cl:21])=[N:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:14][C:15]1[C:16]([N:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:7]([CH3:13])[CH2:8][C:9]([NH:11][CH3:12])=[O:10])=[N:17][C:18]([Cl:21])=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 68683919HCID 68683919, compound2×

Product 1

HCID 86617583HCID 86617583, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of 3-(cyclopentylamino)-N-methyl-butanamide (Intermediate 122; 887 mg, 4.80 mmol), 5-bromo-2,4-dichloropyrimidine (1.15 g, 5.04 mmol) and potassium carbonate (1.34 g, 9.60 mmol) in acetone (20 mL) were heated under reflux conditions to 65° C. for 3 days and then at 75° C. for a further 16 hrs. The solvent was evaporated and the residue taken up in Ethyl Acetate (200 mL) and water (200 mL). The aqueous phase was separated and the organic phase further washed with water (200 mL) and brine (200 mL). The organic phase was evaporated and the residue purified by flash silica chromatography (companion, 40 g, 0-10% MeOH/DCM) followed by base modified preparative HPLC (30-50% gradient) to give the title compound as a yellow solid (117 mg, 6%).

Workup

  1. customThe solvent was evaporated
  2. customThe aqueous phase was separated
  3. washthe organic phase further washed with water (200 mL) and brine (200 mL)
  4. customThe organic phase was evaporated
  5. customthe residue purified by flash silica chromatography (companion, 40 g, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-6989d665c52a413d8f963140627156b9
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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