Potassium Carbonate → HCID 57962490, compound

HRID 541860Notes

Reaction equation

HRID 541860 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[N:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:24][C:25]1[N:30]=[C:29](Cl)[C:28]([Cl:32])=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:24][C:25]1[N:30]=[C:29]([NH:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][C:10]3[N:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH:13]=[CH:12][CH:11]=3)[CH:5]=[CH:6][CH:7]=2)[C:28]([Cl:32])=[CH:27][N:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57961604HCID 57961604, compound

Product 1

HCID 57962490HCID 57962490, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl {6-[2-(3-aminophenyl)ethyl]pyridin-2-yl}carbamate (200 mg, 0.64 mmol) and 2,4,5-trichloropyrimidine (123 mg, 0.67 mmol) in N,N-dimethylformamide (2.9 mL) was added potassium carbonate (264 mg, 1.91 mmol). The resultant mixture was stirred overnight at room temperature. The reaction mixture was filtered first to remove K2CO3, followed by quenching with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and then dried (Na2SO4), filtered and concentrated to give the residue, which was purified by silica gel column chromatography to give the desired product as a light brown gel (231 mg, 79%). LCMS for C17H16Cl2N5 [(M-Boc+H)+H]+: m/z=360.0, 362.0.

Workup

  1. filtrationThe reaction mixture was filtered first
  2. customto remove K2CO3
  3. customby quenching with water
  4. additionEtOAc was added
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with EtOAc twice
  7. washThe combined organic layers were washed with water
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give the residue, which
  12. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-aceaec22f21840e3ab09271a127b3df1
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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