Potassium Carbonate → HCID 57962341, compound

HRID 541875Notes

Reaction equation

HRID 541875 reaction equation
Cl.Cl.[N+:3]([C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][CH:20]=1)[CH2:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=1)([O-:5])=[O:4].[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)C=O>[Cl:21][C:22]1[N:27]=[C:26]([NH:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([NH:10][CH2:9][C:8]3[CH:18]=[CH:19][CH:20]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=3)[CH:12]=2)[C:25]([Cl:29])=[CH:24][N:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 66897337HCID 66897337, compound

Product 1

HCID 57962341HCID 57962341, compoundYield 128.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3-nitrobenzyl)benzene-1,3-diamine dihydrochloride (6.58 g, 0.021 mol) and 2,4,5-trichloropyrimidine (2.38 mL, 0.021 mol) in N,N-dimethylformamide (70 mL) was added potassium carbonate (10.1 g, 0.073 mol). The resultant mixture was stirred for 60 h at room temperature. The reaction mixture was filtered first to remove K2CO3, and then 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 then dried (Na2SO4), filtered and concentrated to give the residue (10.5 g), which was purified by silica gel column chromatography to give the desired product as a light yellow powder (6.19 g, 76%). LCMS for C17H14Cl2N5O2 (M+H)+: m/z=389.9.

Workup

  1. filtrationThe reaction mixture was filtered first
  2. customto remove K2CO3
  3. customquenched with water
  4. additionEtOAc was added
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with EtOAc twice
  7. washThe combined organic layers were washed with water
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-99910323a20140349b3ce0cc7ac3d811
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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