Potassium Carbonate → HCID 57962468, compound

HRID 541803Notes

Reaction equation

HRID 541803 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:20])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:6]=[CH:7][CH:8]=1.[Cl:21][C:22]1[N:27]=[C:26](Cl)[C:25]([Cl:29])=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:21][C:22]1[N:27]=[C:26]([NH:2][C:3]2[CH:4]=[C:5]([NH:9][C:10](=[O:20])[C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)[CH:6]=[CH:7][CH:8]=2)[C:25]([Cl:29])=[CH:24][N:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 66880816HCID 66880816, compound

Product 1

HCID 57962468HCID 57962468, compoundYield 131.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3-aminophenyl)-3-nitrobenzamide hydrochloride (0.200 g, 0.681 mmol) and 2,4,5-trichloropyrimidine (0.071 mL, 0.619 mmol) in DMF (1.6 mL) was added potassium carbonate (0.30 g, 2.2 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 desired product as a light brown powder (330 mg). LCMS for C17H11Cl2N5O3 (M+H)+: m/z=403.9, 405.9, 407.9. 1H NMR (400 MHz, CD3OD): δ 8.82 (t, J=2.0 Hz, 1H), 8.45 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 8.34 (ddd, J=7.6, 2.0, 1.2 Hz, 1H), 8.24 (s, 1H), 7.97 (br, 2H), 7.76 (t, J=8.0 Hz, 1H), 7.56 (m, 1H), 7.43 (ddd, J=8.0, 2.0, 1.2, 1H).

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

Sources & evidence

ORD record
ord-ee5c5640073245ceb6373116b2b2426e
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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