Tetrahydrofuran → HCID 178465289, compound

HRID 1447153Notes

Reaction equation

HRID 1447153 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]=[C:17]([OH:19])[C:16]([C:20]([OH:22])=[O:21])=[CH:15][N:14]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].CN(C)C(=O)C.C(N1C=CN=C1)(N1C=CN=C1)=O.O1CCCC1>CCOCC>[N-:18]1[CH:17]=[CH:16][N:14]=[CH:13]1.[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:18]=[C:17]([OH:19])[C:16]([C:20]([OH:22])=[O:21])=[CH:15][N:14]=2)=[CH:11][CH:12]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 31374DimethylacetamideHCID 682631,1'-Carbonyldiimidazole2×HCID 178465288HCID 178465288, compound

Product 1

HCID 178465289HCID 178465289, compoundYield 210.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 4.6 g (15.2 mmol) of the above pyrimidine acid and 25 ml of N,N-dimethylacetamide is stirred at 0°-5° and 4.9 g (30 mmol) of carbonyldiimidazole is added. The mixture is stirred for 2 hrs as the ice bath melts and another 2.5 g (15 mmol) of carbonyldiimidazole is added. Stirring is continued for 2 hrs and 50 ml of tetrahydrofuran is added and the reaction is refrigerated overnight. A 200 ml portion of ether is added and the precipitated solid is filtered, washed with ether, and dried under high vacuum over phosphorus pentoxide to give 5.9 g of 2-[4-(N-ethylcarbamoylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid imidazolide.

Workup

  1. stirringStirring
  2. waitthe reaction is refrigerated overnight
  3. filtrationthe precipitated solid is filtered
  4. washwashed with ether
  5. dry with materialdried under high vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-52ef602deb55426f99b72d7a84436d82
Source dataset
uspto-grants-1982_02
Patent number
US04315933

Reaction notes

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