Dimethylformamide → HCID 86633965, compound

HRID 1041231Notes

Reaction equation

HRID 1041231 reaction equation
[NH2:1][C:2]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][C:8]#[N:9])=[O:5].[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([Cl:23])=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[Cl-].[NH4+]>>[C:8]([CH2:7][NH:6][C:4](=[O:5])[C:3]1[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[C:2]=1[NH:1][C:18]1[C:19]([Cl:23])=[CH:20][N:21]=[C:16]([Cl:15])[N:17]=1)#[N:9]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 2372592,4,5-TrichloropyrimidineHCID 86633967HCID 86633967, compound

Product 1

HCID 86633965HCID 86633965, compoundYield 14%

Conditions

Temperature
85 °C

Procedure

2-Amino-N-cyanomethyl-3-methyl-benzamide (0.624 g, 0.00330 mol), 2,4,5-Trichloro-pyrimidine (0.605 g, 0.00330 mol) and Potassium carbonate (0.456 g, 0.00330 mol) were dissolved in N,N-Dimethylformamide (10.00 mL, 0.1291 mol) and the reaction was heated at 85° C. and was allowed to stir overnight. The reaction mixture 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 150 mg (14%) of N-Cyanomethyl-2-(2,5-dichloro-pyrimidin-4-ylamino)-3-methyl-benzamide. LC/MS (ESI): 336.07.

Workup

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

Sources & evidence

ORD record
ord-8ff1c18aaa86438bace84c48d6b252ae
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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