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

HRID 541813Notes

Reaction equation

HRID 541813 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:10]=[C:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][CH:14]=1)=[O:6].[Cl:26][C:27]1[N:32]=[C:31](Cl)[C:30]([Cl:34])=[CH:29][N:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:26][C:27]1[N:32]=[C:31]([NH:1][C:2]2[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=2)[C:5]([NH:7][CH2:8][C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])[CH:12]=[CH:13][CH:14]=2)=[O:6])[C:30]([Cl:34])=[CH:29][N:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57962529tert-Butyl (3-{[(3-aminobenzoyl)amino]methyl}phenyl)carbamate

Product 1

HCID 57962338tert-Butyl {3-[({3-[(2,5-dichloropyrimidin-4-yl)amino]benzoyl}amino)methyl]phenyl}carbamateYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl (3-{[(3-aminobenzoyl)amino]methyl}phenyl)carbamate (0.60 g, 1.8 mmol) and 2,4,5-trichloropyrimidine (0.183 mL, 1.6 mmol) in DMF (4.3 mL) was added potassium carbonate (0.331 g, 2.4 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with sat'd NH4Cl and water. EtOAc was added and the layers separated. The aqueous layer was extracted with EtOAc twice. The combined organics were washed with water, dried, filtered and concentrated to give the crude, which was purified by silica gel column chromatography to give the desired product (138 mg, 18%). LCMS for C23H23Cl2N5O3 (M-tBu+H)+: m/z=432.0, 434.0, 436.0. 1H NMR (400 MHz, CD3OD): δ 8.23 (s, 1H), 8.04 (t, J=2.0 Hz, 1H), 7.96 (s, 1H), 7.83 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 7.67 (ddd, J=7.6, 2.4, 1.2 Hz, 1H), 7.48 (m, 2H), 7.21 (t, J=8.0 Hz, 1H), 7.00 (d, J=7.6 Hz, 1H), 4.54 (s, 2H), 1.49 (s, 9H).

Workup

  1. customThe reaction was quenched with sat'd NH4Cl and water
  2. additionEtOAc was added
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with EtOAc twice
  5. washThe combined organics were washed with water
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude, which
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8569934c533d44d5a5bdfa0309aec39a
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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