Imidazole → 2-Imidazolyl-4,6-dichloropyrimidine

HRID 352615Notes

Reaction equation

HRID 352615 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-816e32e2362841278585ad5313373c6b
Source dataset
uspto-grants-2004_06
Patent number
US06747031B2

Reaction notes

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