Lithium borohydride → HCID 57786365, compound

HRID 1628878Notes

Reaction equation

HRID 1628878 reaction equation
[BH4-].[Li+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15]3=[N:16][C:17]4[C:18](=[C:19]([C:24](OC)=[O:25])[CH:20]=[CH:21][C:22]=4[Cl:23])[N:14]3[CH2:13][CH2:12][CH2:11]2)=[C:6]([CH3:28])[CH:5]=1>O1CCCC1>[Cl:23][C:22]1[C:17]2[N:16]=[C:15]3[N:10]([C:7]4[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][C:6]=4[CH3:28])[CH2:11][CH2:12][CH2:13][N:14]3[C:18]=2[C:19]([CH2:24][OH:25])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57785858HCID 57785858, compound

Product 1

HCID 57786365HCID 57786365, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Under nitrogen atmosphere, lithium borohydride (1.00 g, 46.0 mmol) was added to a suspension of methyl 1-(4-bromo-2-methylphenyl)-9-chloro-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (5.0 g, 11.5 mmol) in tetrahydrofuran (70 mL) at 0° C., and the mixture was stirred at 50° C. for 20 h. The reaction mixture was quenched by aqueous saturated ammonium chloride at 0° C., and the mixture extracted with ethyl acetate/tetrahydrofuran. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the crude product of the title compound as a white powder (4.68 g, 11.5 mmol, quant.).

Workup

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

Sources & evidence

ORD record
ord-0e104d1411fc444581077f554cd006bf
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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