Dimethylformamide → HCID 178475077, compound

HRID 1106119Notes

Reaction equation

HRID 1106119 reaction equation
[C:1]([NH:4][C@@H:5]([C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]([OH:22])[C:19]([C:23]([OH:25])=[O:24])=[CH:18][N:17]=2)=[CH:12][CH:11]=1)=[O:8])[CH3:6])(=[O:3])[CH3:2].CN(C)C=O.C(N1C=CN=C1)(N1C=CN=C1)=O>C(#N)C>[N-:21]1[CH:20]=[CH:19][N:17]=[CH:16]1.[C:1]([NH:4][C@@H:5]([C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]([OH:22])[C:19]([C:23]([OH:25])=[O:24])=[CH:18][N:17]=2)=[CH:12][CH:11]=1)=[O:8])[CH3:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 178475076HCID 178475076, compound

Product 1

HCID 178475077HCID 178475077, compoundYield 136.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 11.3 g (32.8 mmol) of the above pyrimidine acid and 160 ml of dimethylformamide is stirred at room temperature and 16.0 g (98.4 mmol) of carbonyldiimidazole is added. After 4 hrs at room temperature the dimethylformamide is evaporated under high vacuum at 45° C. to give an oily residue. Acetonitrile (300 ml) is added and solution is obtained by heating on a steam bath and a solid separates almost immediately. The mixture is cooled and the solid filtered, washed with acetonitrile, and dried to give 9.2 g of the title imidazolide.

Workup

  1. customAfter 4 hrs at room temperature the dimethylformamide is evaporated under high vacuum at 45° C.
  2. customto give an oily residue
  3. customsolution is obtained
  4. temperatureby heating on a steam bath
  5. temperatureThe mixture is cooled
  6. filtrationthe solid filtered
  7. washwashed with acetonitrile
  8. customdried

Sources & evidence

ORD record
ord-d61f723dda0c49b3bfa03bb244ed86f9
Source dataset
uspto-grants-1982_01
Patent number
US04311699

Reaction notes

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