Methanol → HCID 18354395, compound

HRID 429300Notes

Reaction equation

HRID 429300 reaction equation
CS[C:3]1[N:8]=[C:7]([N:9]2[C:13]3[CH:14]=[CH:15][C:16]([N:18]4[CH2:22][CH2:21][N:20]([CH2:23][CH3:24])[C:19]4=[O:25])=[CH:17][C:12]=3[N:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1.[CH3:26]O.O[O:29][S:30]([O-:32])=O.[K+]>O.C(Cl)Cl>[CH3:26][S:30]([C:3]1[N:8]=[C:7]([N:9]2[C:13]3[CH:14]=[CH:15][C:16]([N:18]4[CH2:22][CH2:21][N:20]([CH2:23][CH3:24])[C:19]4=[O:25])=[CH:17][C:12]=3[N:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1)(=[O:32])=[O:29]

Participants

6

Reactant 3

HCID 887MethanolHCID 183544152-Methylthio-4-[5-(3-ethyl-imidazolidin-2-on-1-yl)benzimidazol-1-yl]pyrimidineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18354395HCID 18354395, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-Methylthio-4-[5-(3-ethyl-imidazolidin-2-on-1-yl)benzimidazol-1-yl]pyrimidine (100 mg, 0.282 mmol) in 1:1 methanol:methylene chloride (7 ml) was added a mixture of Oxone® (520 mg, 0.846 mmol) in water (2 ml) at 0° C. The reaction mixture was stirred at it for 7 h, then diluted with methylene chloride. The mixture was separated; the aqueous layer was extracted with methylene chloride (3×50 ml). The combined methylene chloride layer was dried over magnesium sulfate. Removal of the solvent and subsequent purification by preparative thin layer chromatography eluting with 5% 2N ammonium in methanol:methylene chloride system provided 63 mg of the title compound. Mass spectrum (ESI): 387 (M+1).). 1H NMR (CDCl3): δ8.97 (d, J=5.7 Hz, 1H); 8.71 (s, 1H); 8.26 (d, J=9.1 Hz, 1H); 8.02 (dd, J1=8.9 Hz, J2=2.1 Hz, 1H); 7.85 (d, J=2.0 Hz, 1H); 7.74 (d, J=5.7 Hz, 1H); 3.93 (t, J=8.0 Hz, 2H); 3.56 (t, J=8.0 Hz, 2H); 3.45 (s, 3H); 3.42(q, J=7.3Hz, 2H); 1.23 (t, J=7.3 Hz, 3H).

Workup

  1. customThe mixture was separated
  2. extractionthe aqueous layer was extracted with methylene chloride (3×50 ml)
  3. dry with materialThe combined methylene chloride layer was dried over magnesium sulfate
  4. customRemoval of the solvent and subsequent purification by preparative thin layer chromatography
  5. washeluting with 5% 2N ammonium in methanol

Sources & evidence

ORD record
ord-314ad08f73ff4084b44cdd1b08b4094d
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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