Potassium Carbonate → tert-Butyl {3-[({3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}sulfonyl)amino]phenyl}carbamate

HRID 541827Notes

Reaction equation

HRID 541827 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][S:6]([NH:9][C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=1)(=[O:8])=[O:7].[Cl:27][C:28]1[N:33]=[C:32](Cl)[C:31]([Cl:35])=[CH:30][N:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:27][C:28]1[N:33]=[C:32]([NH:1][C:2]2[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=2)[CH2:5][S:6]([NH:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=2)(=[O:8])=[O:7])[C:31]([Cl:35])=[CH:30][N:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57961598tert-Butyl (3-{[(3-aminobenzyl)sulfonyl]amino}phenyl)carbamate

Product 1

HCID 57962160tert-Butyl {3-[({3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}sulfonyl)amino]phenyl}carbamateYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl (3-{[(3-aminobenzyl)sulfonyl]amino}phenyl)carbamate (0.64 g, 1.7 mmol) and 2,4,5-trichloropyrimidine (0.28 g, 1.5 mmol) in DMF (5 mL) was added potassium carbonate (0.26 g, 1.8 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with sat'd NH4Cl and water. EtOAc was then added and the layers separated. The aqueous phase was extracted with EtOAc. The combined organics were washed with water and brine then dried (MgSO4), filtered, and concentrated to give the desired product (0.75 g, 92%). LCMS for C22H23Cl2N5O4S (M-tBu+H)+: m/z=467.9, 469.9.

Workup

  1. customThe reaction was quenched with sat'd NH4Cl and water
  2. additionEtOAc was then added
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washThe combined organics were washed with water and brine
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a4755c17ef374321a1a0a4c6d60b0867
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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