Imidazole → 2-Imidazolyl-4,6-dichloropyrimidine

HRID 2303256Notes

Reaction equation

HRID 2303256 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Cl[C:7]1[C:8]([Cl:14])=[N:9][C:10](Cl)=[N:11][CH:12]=1.C(N(CC)CC)C.[Cl-:22].[NH4+]>C1COCC1>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:10]1[N:11]=[C:12]([Cl:22])[CH:7]=[C:8]([Cl:14])[N:9]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 221700012-Imidazolyl-4,6-dichloropyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

One equivalent of imidazole is added in one portion to a solution of one equivalent of trichloropyrimidine and 1.5 equivs of triethylamine in THF. After reaction is complete, the reaction mixture is poured into saturated, aqueous ammonium chloride and extracted three times with ethyl acetate. The combined organic layers are washed with brine and dried. The reaction mixture is filtered and all volatiles removed under reduced pressure. The product, 2-imidazolyl-4,6-dichloropyrimidine (the compound of formula (VIIIa)) is isolated by flash chromatography (20% ethyl acetate in hexane) as an off-white solid.

Workup

  1. customAfter reaction
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. customdried
  5. filtrationThe reaction mixture is filtered
  6. customall volatiles removed under reduced pressure

Sources & evidence

ORD record
ord-e61cb7c23ca64334ad5fe88262a17eb8
Source dataset
uspto-grants-2002_08
Patent number
US06432947B1

Reaction notes

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