Dimethylformamide → HCID 86633964, compound

HRID 1041228Notes

Reaction equation

HRID 1041228 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH3:9])=[O:5].[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-].[NH4+]>>[Cl:14][C:15]1[N:20]=[C:19]([NH:1][C:2]2[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=2[C:4]([NH:6][CH2:7][CH2:8][CH3:9])=[O:5])[C:18]([Cl:22])=[CH:17][N:16]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 2372592,4,5-TrichloropyrimidineHCID 16533352-amino-N-propylbenzamide

Product 1

HCID 86633964HCID 86633964, compoundYield 64%

Conditions

Temperature
90 °C

Procedure

2-Amino-N-propyl-benzamide (0.360 g, 0.00202 mol), 2,4,5-Trichloro-pyrimidine (0.370 g, 0.00202 mol) and Potassium carbonate (0.837 g, 0.00606 mol) were dissolved in N,N-Dimethylformamide (10.0 mL, 0.129 mol) and the reaction was heated at 90° C. and was allowed to stir overnight. The reaction mixture was then cooled was poured over saturated ammonium chloride, and organics were extracted with ethyl acetate/dichloromethane. Combined organics were dried over sodium sulfate, filtered and reduced en vacuo. The crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate). Combined fractions were reduced en vacuo to afford 420 mg (64%) of 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-propyl-benzamide. LC/MS (ESI): 325.12. 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-butyl-benzamide was made in an analogous fashion replacing 1-aminopropane with 1-aminobutane.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionorganics were extracted with ethyl acetate/dichloromethane
  3. dry with materialCombined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. customThe crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate)

Sources & evidence

ORD record
ord-86abfc1d4aa74eadbba25e31492c1644
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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