Dimethylformamide → HCID 178473129, compound

HRID 1447151Notes

Reaction equation

HRID 1447151 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[C:18]([OH:20])[C:17]([C:21]([OH:23])=[O:22])=[CH:16][N:15]=2)=[CH:10][CH:9]=1)=[O:6])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.CN(C)C=O>CCOCC>[N-:19]1[CH:18]=[CH:17][N:15]=[CH:14]1.[CH2:1]([O:3][C:4](=[O:24])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:19]=[C:18]([OH:20])[C:17]([C:21]([OH:23])=[O:22])=[CH:16][N:15]=2)=[CH:12][CH:13]=1)=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 178473128HCID 178473128, compound

Product 1

HCID 178473129HCID 178473129, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5.96 g (18 mmol) of the above pyrimidine acid, 4.37 g (27 mmol) of carbonyldiimidazole, and 90 ml of dimethylformamide is stirred at 60° for 10 min and at room temperature for 1.5 hrs. The reaction mixture is diluted with 100 ml of ether and the solid filtered, washed with ether, and dried to give 2.52 g of 2-[4-[(2-ethoxy-1,2-dioxoethyl)amino]phenyl]-4-hydroxy-5-pyrimidine carboxylic acid imidazolide. The filtrate is treated with 150 ml of ether and another 1.32 g of imidazolide is obtained.

Workup

  1. filtrationthe solid filtered
  2. washwashed with ether
  3. customdried

Sources & evidence

ORD record
ord-1bb61087ef744230a931055d73a0b8ff
Source dataset
uspto-grants-1982_02
Patent number
US04315933

Reaction notes

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