Potassium Carbonate → HCID 58467874, compound

HRID 1614983Notes

Reaction equation

HRID 1614983 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[C:7]([CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:14]=[N:15][CH:16]=2)[CH:8]=1.[Cl:33][C:34]1[N:39]=[C:38](Cl)[C:37]([Cl:41])=[CH:36][N:35]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:29]([O:28][C:26]([NH:25][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:36]2[C:37]([Cl:41])=[CH:38][N:39]=[C:34]([Cl:33])[N:35]=2)=[CH:8][C:7]=1[CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:21])[CH3:22])[CH:14]=[N:15][CH:16]=1)=[O:27])([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 58467865tert-Butyl [5-(2-{5-(aminomethyl)-2-[(tert-butoxycarbonyl)amino]phenyl}ethyl)pyridin-3-yl]carbamate

Product 1

HCID 58467874HCID 58467874, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl [5-(2-{5-(aminomethyl)-2-[(tert-butoxycarbonyl)amino]phenyl}ethyl)pyridin-3-yl]carbamate (0.81 g, 1.8 mmol) and 2,4,5-trichloropyrimidine (0.45 g, 2.4 mmol) in N,N-dimethylformamide (10 mL) was added potassium carbonate (1.30 g, 9.37 mmol). The resultant mixture was stirred overnight at 45° C. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc once. The combined organic layers were washed with water, and then dried (Na2SO4), filtered, and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired product as a white powder (0.44 g, 40%). LCMS for C28H35Cl2N6O4 (M+H)+: m/z=589.1, 591.1.

Workup

  1. customThe reaction was quenched with water
  2. additionEtOAc was added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc once
  5. washThe combined organic layers were washed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7bc2045fbc984578a59e5a05ae730c36
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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