Potassium Carbonate → Methyl 3-(2-{3-[(tert-butoxycarbonyl)amino]phenyl}ethyl)-5-[(2,5-dichloropyrimidin-4-yl)amino]benzoate

HRID 541741Notes

Reaction equation

HRID 541741 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:24]=2)[CH:20]=1)[C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.Cl>[C:33]([O:32][C:30]([NH:29][C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][C:19]2[CH:18]=[C:13]([CH:12]=[C:11]([NH:10][C:6]3[C:5]([Cl:9])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])[CH:28]=[CH:27][CH:26]=1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57961977Methyl 3-amino-5-(2-{3-[(tert-butoxycarbonyl)amino]phenyl}ethyl)benzoate

Product 1

HCID 57962027Methyl 3-(2-{3-[(tert-butoxycarbonyl)amino]phenyl}ethyl)-5-[(2,5-dichloropyrimidin-4-yl)amino]benzoateYield 72%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2,4,5-trichloropyrimidine (0.371 mL, 3.24 mmol) and methyl 3-amino-5-(2-{3-[(tert-butoxycarbonyl)amino]phenyl}ethyl)benzoate (1.20 g, 3.24 mmol) in DMF (20 mL) and potassium carbonate (895 mg, 6.48 mmol) were stirred at 60° C. overnight. The reaction mixture was diluted with 1 N HCl and extracted with ethyl acetate three times. The combined organic solutions were dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (1.20 g, 72%). LCMS for C25H26Cl2N4O4Na (M+Na)+: m/z=539.3, 541.3.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe combined organic solutions were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-dd60adeda7de45caa2b2a12d3987e532
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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