Sodium borohydride → HCID 57786343, compound

HRID 1399077Notes

Reaction equation

HRID 1399077 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:12]2[N:11]=[C:10]3[N:13]([C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=4[Cl:24])[CH2:14][CH2:15][CH2:16][N:9]3[C:8]=2[C:7]([CH:25]([CH2:28][CH3:29])[CH:26]=[O:27])=[CH:6][CH:5]=1>O1CCCC1>[Cl:3][C:4]1[C:12]2[N:11]=[C:10]3[N:13]([C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=4[Cl:24])[CH2:14][CH2:15][CH2:16][N:9]3[C:8]=2[C:7]([CH:25]([CH2:28][CH3:29])[CH2:26][OH:27])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57786157HCID 57786157, compound

Product 1

HCID 57786343HCID 57786343, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (13.5 mg, 0.357 mmol) was added to a stirred solution of 2-[9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]butanal (151 mg, 0.357 mmol) in tetrahydrofuran (3.0 mL) at 0° C., and the mixture was stirred at 0° C. for 2 hr. The reaction was quenched by aqueous saturated ammonium chloride at 0° C. and the mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was recrystallized from ethanol/ethyl acetate to give the title compound as a colorless crystal (143 mg, 0.337 mmol, 94%).

Workup

  1. customThe reaction was quenched by aqueous saturated ammonium chloride at 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-85a4cf2dc30842d6b43c45b3a8df5a0f
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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