HCID 18375789, compound → HCID 18375629, compound

HRID 2300822Notes

Reaction equation

HRID 2300822 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:13]3[CH:14]=[C:15]([C:18](N(C)OC)=[O:19])[CH:16]=[CH:17][C:12]=3[N:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1.[CH3:24][Mg+].[Br-]>C(Cl)Cl>[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:13]3[CH:14]=[C:15]([C:18]([CH3:24])=[O:19])[CH:16]=[CH:17][C:12]=3[N:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 18375789HCID 18375789, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 18375629HCID 18375629, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methylthio-4-[6-(N-methyl-N-methoxyaminocarbonyl)benzimidazol-1-yl]pyrimidine (26 mg, 0.079 mmol) in CH2Cl2 (0.8 mL) at 0° C. was added CH3MgBr (255 μL, 1.4M) dropwise and stirred for 3 h at 0° C. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with CH2Cl2. The combined extracts were washed with brine and dried over Na2SO4. The crude material was purified by preparative thin layer chromatography eluting with 3% MeOH/CH2Cl2 to obtain 15.7 mg of the title compound. Partial 1H NMR (500 MHz, CDCl3): δ 8.94 (s, 1H); 8.79 (s, 1H); 8.67 (d, J=5.0 Hz, 1H); 8.04 (d, J=7.5 Hz, 1H); 7.9 (d, J=7.5 Hz, 1H); 7.28 (d, J=5.0 Hz, 1H); 2.74 (s, 6H).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NH4Cl
  2. extractionextracted with CH2Cl2
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe crude material was purified by preparative thin layer chromatography
  6. washeluting with 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-fb11364029c44b4b886c0b7d5af307ce
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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