Dimethylformamide → HCID 58296315, compound

HRID 390041Notes

Reaction equation

HRID 390041 reaction equation
[C:1](N)(=O)C1C=CC=CC=1.[CH3:10][C:11]1[C:16]([C:17]([NH2:19])=[O:18])=[C:15]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([S:27][CH3:28])=[CH:23][CH:22]=2)[N:14]=[C:13]([S:29][CH3:30])[N:12]=1.[CH3:31][N:32]([CH:34]=O)[CH3:33]>>[CH3:31][N:32]([CH3:34])/[CH:33]=[CH:10]/[C:11]1[N:12]=[C:13]([S:29][CH3:30])[N:14]=[C:15]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([S:27][CH3:28])=[CH:23][CH:22]=3)[CH:1]=[N:19][C:17](=[O:18])[C:16]=12

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 67219618HCID 67219618, compound

Product 1

HCID 58296315HCID 58296315, compoundYield 72%

Procedure

To a solution of 4-methyl-2-(methylthio)-6-{[4-(methylthio)phenyl]amino}-5-pyrimidinecarboxamide benzamide (0.50 g, 1.57 mmol) in DMF (20 ml) was added dimethylormamide-dimethylacetal (0.56 g, 4.7 mmol), and the reaction mixture was stirred at 85° for 1.5 h. It was cooled to room temperature and DMF was removed under vacuum. The residue was chromatographed (silica gel, eluting with hexane to ethyl acetate gradient followed by 10% methanol in methylene chloride) to yield the product (0.43 g, 72% yield).

Workup

  1. customDMF was removed under vacuum
  2. customThe residue was chromatographed
  3. wash(silica gel, eluting with hexane to ethyl acetate gradient followed by 10% methanol in methylene chloride)

Sources & evidence

ORD record
ord-73c18991f1494bf7bb87bfbaf35db393
Source dataset
uspto-grants-2013_02
Patent number
US08383635B2

Reaction notes

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