Dimethyl Sulfoxide → HCID 136332407, compound

HRID 629042Notes

Reaction equation

C(=O)([O-])O.[Na+].CS(C)=O.Cl.[NH2:11][OH: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]>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:11][OH:12])[NH2:33])=[N:28][CH:29]=1)[CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 40 °C

Procedure

Process 2: Sodium hydrogen carbonate (2.02 mg, 24.0 mmol) was added to dimethyl sulfoxide solution (20 mL) of hydroxylamine hydrochloride (1.42 g, 20.4 mmol) and stirred for 1 hour at 40° C. Dimethyl sulfoxide solution (3 mL) 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) was added to the reaction mixture and stirred for 19 hours at 90° C. The reaction mixture 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 obtained residues were subjected to silica gel column chromatography (ethyl acetate) to give 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

stirringstirred for 19 hours at 90° C
extractionextracted with ethyl acetate
washwashed with water and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9f881af629a04ea49680c2a168a9f72f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315493B2

Reaction notes

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