Benzimidazole → HCID 18375460, compound

HRID 2300832Notes

Reaction equation

HRID 2300832 reaction equation
[H-].[Na+].[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH:4]=1.[CH2:12]([S:14][C:15]1[N:20]=[C:19](Cl)[CH:18]=[C:17]([CH2:22][CH2:23][CH3:24])[N:16]=1)[CH3:13]>CN(C=O)C>[CH2:12]([S:14][C:15]1[N:20]=[C:19]([N:3]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=[CH:4]2)[CH:18]=[C:17]([CH2:22][CH2:23][CH3:24])[N:16]=1)[CH3:13]

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 24758Sodium hydrideHCID 183758132-Ethylthio4-chloro-6-propylpyrimidine

Product 1

HCID 18375460HCID 18375460, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (76 mg) in DMF (2 mL) was added benzimidazole, and this was followed by addition of 2-ethylthio4-chloro-6-propylpyrimidine dissolved in DMF (3 mL). The reaction mixture was then placed in a 100° C. oil bath. After 1 h, the reaction was cooled to room temperature, quenched with 5 mL of water and extracted with ethyl acetate. The organic layer was washed with saturated NaCl and dried (anhydrous Na2SO4). Removal of solvent followed by purification on silica gel column (9% acetone/hexane) provided 390 mg of the title compound. Mass spectrum (CI) 298 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.69 (s, 1H); 8.17 (d, J=7.6 Hz, 1H); 7.88 (d, J=7.8 Hz, 1H); 7.42 (m, 2H); 7.05 (s, 1H); 3.27 (q, J=7.4 Hz, 2H); 2.78 (t, J=7.5 Hz, 2H); 1.85 (m, 2H); 1.49 (t, J=7.3 Hz, 3H); 1.05 (t, J=7.3 Hz, 3H).

Workup

  1. customwas then placed in a 100° C.
  2. customquenched with 5 mL of water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated NaCl
  5. dry with materialdried (anhydrous Na2SO4)
  6. customRemoval of solvent
  7. customfollowed by purification on silica gel column (9% acetone/hexane)

Sources & evidence

ORD record
ord-a7b1692bdf384160aefb934b55333ca6
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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