Potassium Carbonate → HCID 58467875, compound

HRID 1614952Notes

Reaction equation

HRID 1614952 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][CH2:12][NH2:13])[CH:7]=[CH:8][CH:9]=1.[Cl:14][C:15]1[N:20]=[C:19](Cl)[C:18]([Cl:22])=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:14][C:15]1[N:20]=[C:19]([NH:13][CH2:12][CH2:11][CH2:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH3:2])[CH:5]=2)[C:18]([Cl:22])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 30298083-(3-Methoxyphenyl)propan-1-amine hydrochloride

Product 1

HCID 58467875HCID 58467875, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(3-methoxyphenyl)propan-1-amine hydrochloride (2.00 g, 9.92 mmol) and 2,4,5-trichloropyrimidine (1.19 mL, 10.4 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (4.80 g, 34.7 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 (then triturated with cold EtOAc) to give the desired product as a light brown gel (2.82 g, 91%). LCMS for C14H16Cl2N3O (M+H)+: m/z=312.0, 314.0.

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. customthen triturated with cold EtOAc)

Sources & evidence

ORD record
ord-b00902ac255049af941d30ae2a6494da
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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