Triethylamine → HCID 178430861, compound

HRID 1822767Notes

Reaction equation

HRID 1822767 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.Cl[C:8]1[C:9]([Cl:15])=[N:10][C:11](Cl)=[N:12][CH:13]=1.C(N(CC)CC)C.[Cl-:23].[NH4+]>C1COCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[N:12]=[C:13]([Cl:23])[CH:8]=[C:9]([Cl:15])[N:10]=2)[NH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2372592,4,5-TrichloropyrimidineHCID 178418800HCID 178418800, compound

Product 1

HCID 178430861HCID 178430861, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Methylimidazole (11.45 g, 140 mmol) was added in one portion to a solution of trichloropyrimidine in (2.47 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-(4-methylimidazolyl)-4,6-dichloropyrimidine was isolated by flash chromatography (15% ethyl acetate in hexane) as an off-white solid.

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-8314abc33e1146fa94d34a3ce1ddef59
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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