Imidazole → HCID 66318428, compound

HRID 871144Notes

Reaction equation

HRID 871144 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Cl[C:9]1[C:14]([I:15])=[CH:13][N:12]=[CH:11][N:10]=1>C1COCC1>[N:1]1([C:9]2[C:14]([I:15])=[CH:13][N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 112302044-Chloro-5-iodopyrimidine

Product 1

HCID 66318428HCID 66318428, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1H-imidazole (0.085 g, 1.248 mmol) in THF (Volume: 10 mL) was added sodium hydride (0.062 g, 1.560 mmol). After 15 minutes at room temperature, 4-chloro-5-iodopyrimidine (0.25 g, 1.040 mmol) was added as a solution in THF (5 mL). After 2 h at room temperature, the reaction was quenched with water. The reaction mixture was extracted with EtOAc (3×). The combined organics were dried over MgSO4, filtered and concentrated to give the title compound (0.155 g, 0.541 mmol, 52.1% yield) as a pale yellow solid. ESI MS (M+H)+=273.0.

Workup

  1. waitAfter 2 h at room temperature
  2. customthe reaction was quenched with water
  3. extractionThe reaction mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e821aa34f2bc4411a1b560a0c93c2c5b
Source dataset
uspto-grants-2015_03
Patent number
US08969586B2

Reaction notes

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