Diisopropylethylamine → Benzimidazole

HRID 2036556Notes

Reaction equation

HRID 2036556 reaction equation
N[C:2]1[C:7]([C:8]#N)=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:11][CH2:12]N(C(C)C)C(C)C>C(O)CCC.O.CCOC(C)=O.CCCCCC>[N:3]1[C:2]2[CH:7]=[CH:8][CH:11]=[CH:12][C:6]=2[NH:5][CH:4]=1

Participants

6

Reactant 2

HCID 81531DiisopropylethylamineHCID 122782624-Amino-6-chloropyrimidine-5-carbonitrile

Product 1

HCID 5798Benzimidazole

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
120 °C

Procedure

Synthesis of D-7. A mixture of 4-amino-6-chloropyrimidine-5-carbonitrile (B) (0.257 g, 1.662 mmol), D-6 (1.662 mmol), and DIEA (0.868 mL, 4.99 mmol) in n-butanol (16.62 mL) was stirred at 120° C. After 24 h, the heat was removed and left at rt. After cooling, the mixture was concentrated under reduced pressure to give a brown solid, which was suspended in water (50 mL), sonicated, filtered, and washed with water (100 mL) to give a tan solid. The tan solid was suspended in EtOAc-hexane (1:4, 20 mL), filtered, washed with EtOAc-hexane (1:4, 20 mL), and dried to give D-7 as a racemic mixture.

Workup

  1. customSynthesis of D-7
  2. customthe heat was removed
  3. waitleft at rt
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated under reduced pressure
  6. customto give a brown solid, which
  7. customsonicated
  8. filtrationfiltered
  9. washwashed with water (100 mL)
  10. customto give a tan solid
  11. filtrationfiltered
  12. washwashed with EtOAc-hexane (1:4, 20 mL)
  13. customdried
  14. customto give D-7 as a racemic mixture

Sources & evidence

ORD record
ord-0789e2d6b4f947b0b57d7205c251fc85
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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