Potassium Carbonate → HCID 57961668, compound

HRID 541800Notes

Reaction equation

HRID 541800 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:12][CH:13]=1)=[O:6].[Cl:25][C:26]1[N:31]=[C:30](Cl)[C:29]([Cl:33])=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:25][C:26]1[N:31]=[C:30]([NH:1][C:2]2[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=2)[C:5]([NH:7][C:8]2[CH:9]=[C:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:18])[CH3:19])[CH:11]=[CH:12][CH:13]=2)=[O:6])[C:29]([Cl:33])=[CH:28][N:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57961539HCID 57961539, compound

Product 1

HCID 57961668HCID 57961668, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl {3-[(3-aminobenzoyl)amino]phenyl}carbamate (0.500 g, 1.53 mol) and 2,4,5-trichloropyrimidine (0.25 g, 1.4 mmol) in DMF (3.7 mL) was added potassium carbonate (0.29 g, 2.1 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with saturated (sat'd) NH4Cl and water. EtOAc was added and the layers separated. The aqueous layer was extracted with EtOAc twice and the combined organics were washed with water, dried, filtered and concentrated to give 800 mg of crude product, which was purified by Combi-Flash column chromatography (12 g column, 0 to 30% EtOAc in hexane) to give the desired product (66 mg, 10%). LCMS for C22H21Cl2N5O3 (M-tBu+H)+: m/z=420.0, 418.1. 1H NMR (400 MHz, CD3OD): δ 8.26 (s, 1H), 8.11 (t, J=2.0 Hz, 1H), 7.89 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 7.85 (t, J=2.0 Hz, 1H), 7.74 (ddd, J=7.6, 2.0, 0.8 Hz, 1H), 7.53 (t, J=8.0 Hz, 1H), 7.32 (dd, J=8.0, 1.2 Hz, 1H), 7.24 (t, J=8.0 Hz, 1H), 7.19 (m, 1H), 1.52 (s, 9H).

Workup

  1. customThe reaction was quenched with saturated (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 800 mg of crude product, which
  10. customwas purified by Combi-Flash column chromatography (12 g column, 0 to 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-d63a842b8b4d45a683872040d8a05653
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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