Imidazole → 2-Imidazolyl-4,6-dichloropyrimidine

HRID 1760401Notes

Reaction equation

HRID 1760401 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

Imidazole (9.5 g, 140 mmol) was added in one portion to a solution of trichloropyrimidine (24.7 g, 135 mmol) and triethylamine (30 mL, 216 mmol) in THF (500 mL). After 16 hrs, the reaction mixture was poured into saturated, aqueous ammonium chloride and extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over MgSO4. The reaction mixture was filtered and all volatiles were removed under reduced pressure. 2-imidazolyl-4,6-dichloropyrimidine (the compound of formula (VIIIa)) (9.61 g, 33%) was isolated by flash chromatography (20% ethyl acetate in hexane) as an off-white solid. 1H NMR: (CDCl3) δ 7.13 (s, 1), 7.25 (s, 1), 7.76 (s, 1), 8.50 (s, 1).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationThe reaction mixture was filtered
  5. customall volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-4bf1ac712f7e40b3a3440467b116caaa
Source dataset
uspto-grants-2005_01
Patent number
US06841674B2

Reaction notes

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