Dimethylformamide → HCID 178517381, compound

HRID 1348543Notes

Reaction equation

HRID 1348543 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH:10]([C:16]([O:18]CC)=O)[C:11]([O:13]CC)=O.Cl.[NH2:22][C:23]1[NH:24][CH:25]=[CH:26][N:27]=1.C1CCN2C(=NCCC2)CC1.CN(C)C=O>O.C(Cl)(Cl)Cl>[OH:18][C:16]1[N:24]2[CH:25]=[CH:26][N:27]=[C:23]2[N:22]=[C:11]([OH:13])[C:10]=1[C:3]1[C:4]([F:9])=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2782662Propanedioic acid, 2-(2,4,6-trifluorophenyl)-, 1,3-diethyl esterHCID 122112381H-Imidazol-2-amine hydrochloride

Product 1

HCID 178517381HCID 178517381, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.90 g of diethyl (2,4,6-trifluorophenyl)malonate, 2.39 g of 2-aminoimidazole hydrochloride, 4.57 g of DBU and 10 ml of N,N-dimethylformamide was heated at 100° C. for 6 hours. After allowing the reaction mixture to cool to room temperature, chloroform and water were added thereto. The separated water layer was concentrated, the residue was diluted with water and conc. hydrochloric acid was added thereto under ice-cooling. The precipitation was filtered and dried to give 2.2 g of 5,7-dihydroxy-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine.

Workup

  1. temperatureto cool to room temperature
  2. concentrationThe separated water layer was concentrated
  3. additionthe residue was diluted with water and conc. hydrochloric acid
  4. additionwas added
  5. temperatureunder ice-cooling
  6. customThe precipitation
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-3548f248f23c401e85b4ee7b9c5386b4
Source dataset
uspto-grants-2007_05
Patent number
US07211545B2

Reaction notes

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