Potassium Carbonate → HCID 58467890, compound

HRID 1614933Notes

Reaction equation

HRID 1614933 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1.[Cl:17][C:18]1[N:23]=[C:22](Cl)[C:21]([Cl:25])=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:12]([O:11][C:10](=[O:16])[NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][NH:1][C:20]2[C:21]([Cl:25])=[CH:22][N:23]=[C:18]([Cl:17])[N:19]=2)[CH:4]=1)([CH3:13])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 27564813-(Aminomethyl)-1-N-Boc-aniline

Product 1

HCID 58467890HCID 58467890, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl [3-(aminomethyl)phenyl]carbamate (0.50 g, 2.2 mmol) and 2,4,5-trichloropyrimidine (0.45 g, 2.5 mmol) in N,N-dimethylformamide (6 mL) was added potassium carbonate (0.62 g, 4.5 mmol). The resultant mixture was stirred overnight at room temperature. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, and concentrated. The resulted residue was triturated with methylene chloride and hexanes to give the desired product as an off-white powder (0.75 g, 90%). LCMS for C12H11Cl2N4O2 (M-tBu+H)+: m/z=313.0, 315.0.

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 twice
  5. washThe combined organic layers were washed with water and brine successively
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulted residue was triturated with methylene chloride and hexanes

Sources & evidence

ORD record
ord-219adb2c59f2405cb3f5b9dde405504a
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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