Sodium hydride → HCID 22288415, compound

HRID 968250Notes

Reaction equation

HRID 968250 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:14][C:15]1[N:20]=[C:19](Cl)[CH:18]=[CH:17][N:16]=1>C1COCC1>[Cl:14][C:15]1[N:20]=[C:19]([N:11]2[CH:10]=[CH:9][N:8]=[C:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 695912-PhenylimidazoleHCID 775312,4-Dichloropyrimidine

Product 1

HCID 22288415HCID 22288415, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-phenylimidazole (1-2, 484 mg, 3.36 mmol) in dry THF (15 mL) was added NaH (130 mg, 60% dispersion in mineral oil, 3.36 mmol) at room temperature. After gas evolution had ceased, 2,4-dichloropyrimidine (3-1, 0.5 g, 3.36 mmol) was added. The mixture was heated to 50° C. After 18 hours the mixture was cooled to room temperature, quenched with saturated NH4Cl, and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (50% EtOAc/hexanes) gave 2-chloro-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine as a gum. 1H-NMR (300 MHz, CDCl3) δ 8.40 (d, J=5.38 Hz, 1H), 7.80 (s, 1H), 7.45 (m, 5H), 7.25 (s, 1H), 6.68 (d, J=5.38 Hz, 1H).

Workup

  1. temperatureAfter 18 hours the mixture was cooled to room temperature
  2. customquenched with saturated NH4Cl
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b475ead674f1455aa6684c5de97e8324
Source dataset
uspto-grants-2005_10
Patent number
US06958340B2

Reaction notes

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