Water → 2-Ethanesulfonyl-4-[benzimidazol-1-yl]-6-propylpyrimidine

HRID 2300833Notes

Reaction equation

HRID 2300833 reaction equation
[CH2:1]([S:3][C:4]1[N:9]=[C:8]([N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=[CH:11]2)[CH:7]=[C:6]([CH2:19][CH2:20][CH3:21])[N:5]=1)[CH3:2].[OH:22]OS([O-])=O.[K+].[OH2:28]>CO>[CH2:1]([S:3]([C:4]1[N:9]=[C:8]([N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=[CH:11]2)[CH:7]=[C:6]([CH2:19][CH2:20][CH3:21])[N:5]=1)(=[O:22])=[O:28])[CH3:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 183754602-Ethylthio-4-[benzimidazol-1-yl]-6-propylpyrimidineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 183755232-Ethanesulfonyl-4-[benzimidazol-1-yl]-6-propylpyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-ethylthio-4-[benzimidazol-1-yl]-6-propylpyrimidine in MeOH (4 mL) was added a suspension of Oxone® (1.73 g) in water (4 mL). The resulting slurry was stirred at room temperature for 3.5 h. The reaction was diluted with water (10 mL) and extracted with methylene chloride (3×30 mL). The combined organic layer was washed with water, brine and dried (anhydrous Na2SO4). Removal of solvent gave 295 mg of the title compound which was used directly in the next step. 1H NMR (500 MHz, CDCl3): δ 8.76 (s, 1H); 8.37 (d, J=8.0 Hz, 1H); 7.89 (d, J=8.1 Hz, 1H); 7.57 (s, 1H); 7.51 (dd, J=7.3, 8.3 Hz, 1H); 7.46 (dd, J=7.3, 7.6 Hz, 1H); 7.28 (s, 1H); 3.64 (q, J=7.4 Hz, 2H); 2.99 (t, J=7.5 Hz, 2H); 1.92 (m, J=7.5 Hz, 2H); 1.52 (t, J=7.5 Hz, 3H); 1.08 (t, J=7.3 Hz, 3H).

Workup

  1. extractionextracted with methylene chloride (3×30 mL)
  2. washThe combined organic layer was washed with water, brine
  3. dry with materialdried (anhydrous Na2SO4)
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-229ef3a8c25b478995ff898cc0600bb5
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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