Dimethylformamide → HCID 178516173, compound

HRID 2286623Notes

Reaction equation

HRID 2286623 reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:21]=[C:20]([OH:22])[C:19]([C:23]([OH:25])=[O:24])=[CH:18][N:17]=3)=[CH:12][CH:11]=2)=[O:8])[CH2:4][CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.CN(C)C=O.C(#N)C>CCOCC>[N-:21]1[CH:20]=[CH:19][N:17]=[CH:16]1.[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[N:21]=[C:20]([OH:22])[C:19]([C:23]([OH:25])=[O:24])=[CH:18][N:17]=3)=[CH:14][CH:15]=2)=[O:8])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 682631,1'-CarbonyldiimidazoleHCID 178516172HCID 178516172, compound

Product 1

HCID 178516173HCID 178516173, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 13.3 g (38.85 mmol) of the above pyrimidine acid, 12.59 g (77.7 mmol) of carbonyldiimidazole and 100 ml of dimethylformamide is stirred at 54°-59° C. for 1/2 hr and at room temperature for 16 hrs. Acetonitrile (100 ml) and ether (100 ml) are added to the reaction solution. The precipitated solid is filtered, washed with ether, and dried to yield 7.7 g of the title imidazolide.

Workup

  1. filtrationThe precipitated solid is filtered
  2. washwashed with ether
  3. customdried

Sources & evidence

ORD record
ord-abab2fb3f75c4991bfd7a8ffd84db833
Source dataset
uspto-grants-1981_05
Patent number
US04267180

Reaction notes

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