Dimethylformamide → HCID 86633965, compound

HRID 1687536Notes

Reaction equation

HRID 1687536 reaction equation
NC1C(C)=CC=CC=1C(NCC#N)=O.[C:15]([CH2:17][NH:18][C:19](=[O:36])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:21]=1[NH:27][C:28]1[C:33]([Cl:34])=[CH:32][N:31]=[C:30]([Cl:35])[N:29]=1)#[N:16].ClC1N=C(Cl)C(Cl)=CN=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[Cl-].[NH4+]>>[C:15]([CH2:17][NH:18][C:19](=[O:36])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:21]=1[NH:27][C:28]1[C:33]([Cl:34])=[CH:32][N:31]=[C:30]([Cl:35])[N:29]=1)#[N:16]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 2372592,4,5-TrichloropyrimidineHCID 86633966HCID 86633966, compound

Product 1

HCID 86633965HCID 86633965, compoundYield 14%

Conditions

Temperature
85 °C

Procedure

N-Cyanomethyl-2-(2,5-dichloro-pyrimidin-4-ylamino)-3-methyl-benzamide 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-2db44a1fc2c54a17a34c2fb5a3c9583d
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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