Dimethyl Sulfoxide → HCID 136332407, compound

HRID 1622978Notes

Reaction equation

HRID 1622978 reaction equation
C(=O)([O-])O.[Na+].CS(C)=O.Cl.[OH:11][NH2:12].[CH2:13]([C:17]1[N:18]=[C:19]([CH3:45])[N:20]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[C:21](=[O:38])[C:22]=1[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=2[C:32]#[N:33])=[N:28][CH:29]=1)[CH2:14][CH2:15][CH3:16]>C(OCC)(=O)C.O>[CH2:13]([C:17]1[N:18]=[C:19]([CH3:45])[N:20]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[C:21](=[O:38])[C:22]=1[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=2[C:32](=[N:12][OH:11])[NH2:33])=[N:28][CH:29]=1)[CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 67979476HCID 67979476, compound

Product 1

HCID 136332407HCID 136332407, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Process 2: Sodium hydrogen carbonate (2.02 mg, 24.0 mmol) was added to a dimethyl sulfoxide (20 mL) solution of hydroxyl amine hydrochloride (1.42 g, 20.4 mmol), and the reaction solution was stirred at 40° C. for 1 hour. The reaction solution was added a dimethyl sulfoxide (3 mL) solution of 2-{5-{[4-butyl-2-methyl-6-oxo-1-(pyridin-2-yl)-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}benzonitrile (430 mg, 0.987 mmol), and stirred at 90° C. for 19 hours. The reaction solution was added water and extracted with ethyl acetate. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residues obtained were subjected to silica gel column chromatography (ethyl acetate), to obtain 2-{5-{[4-butyl-2-methyl-6-oxo-1-(pyridin-2-yl)-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}-N′-hydroxybenzimidamide (430 mg, 93%) as a white solid.

Workup

  1. stirringstirred at 90° C. for 19 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residues obtained

Sources & evidence

ORD record
ord-84f366cb3906481cad841d934850766b
Source dataset
uspto-grants-2014_07
Patent number
US08778954B2

Reaction notes

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