Lithium borohydride → HCID 57785980, compound

HRID 1628716Notes

Reaction equation

HRID 1628716 reaction equation
[BH4-].[Li+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:26](OC)=[O:27])=[C:8]2[C:12]=1[N:11]=[C:10]1[N:13]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([Cl:24])=[CH:19][C:18]=3[Cl:25])[CH2:14][CH2:15][CH2:16][N:9]21>O1CCCC1>[Cl:3][C:4]1[C:12]2[N:11]=[C:10]3[N:13]([C:17]4[C:22]([CH3:23])=[CH:21][C:20]([Cl:24])=[CH:19][C:18]=4[Cl:25])[CH2:14][CH2:15][CH2:16][N:9]3[C:8]=2[C:7]([CH2:26][OH:27])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57786000HCID 57786000, compound

Product 1

HCID 57785980HCID 57785980, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Lithium borohydride (205 mg, 9.42 mmol) was added to a stirred solution of methyl 9-chloro-1-(2,4-dichloro-6-methylphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (800 mg, 1.88 mmol) in tetrahydrofuran (4.0 mL) at room temperature, and the mixture was stirred at 50° C. for 13 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 washed with ethyl acetate/diisopropyl ether to give the title compound as a colorless powder (620 mg, 1.56 mmol, 83%).

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. washThe residue was washed with ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-4145e2bb57c549888419dec12e826ab5
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

Loading…