Benzimidazole → HCID 15549639, compound

HRID 429277Notes

Reaction equation

HRID 429277 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.Cl[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=1>CN(C=O)C>[CH3:20][S:19][C:15]1[N:16]=[C:17]([N:3]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=[CH:4]2)[CH:18]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 24758Sodium hydrideHCID 971134-Chloro-2-methylthiopyrimidine

Product 1

HCID 15549639HCID 15549639, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of NaH (0.548 mg, 22.8 mmol), benzimidazole (0.52 g, 21.3 mmol) and 4-chloro-2-methylthiopyrimidine (2.48 mL, 21.3 mmol) in 30 mL of DMF was heated to 100° C. for 30 min. The reaction was quenched with H2O and extracted with EtOAc. The combined organic fractions were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography (silica, 0-10% MeOH:CH2Cl2) to give 1.99 g of the title compound. 1H NMR (500 MHz, CDCl3): δ8.69 (s, 1H); 8.64 (d, J=5.5 Hz, 1H); 8.22 (dd, J=1.4, 7.3 Hz); 7.89 (dd, J=1.6, 7.3 Hz); 7.44 (m, 2H); 7.23 (d, J=5.7 Hz, 1H); 2.69 (s, 3H).

Workup

  1. customThe reaction was quenched with H2O
  2. extractionextracted with EtOAc
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (silica, 0-10% MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-e70892bc78fc4098bf3e45a0debec893
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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