Lithium borohydride → HCID 57785932, compound

HRID 1399168Notes

Reaction equation

HRID 1399168 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:24](OC)=[O:25])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[C:16]([CH3:23])=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[CH2:12][CH2:13][CH2:14][N:7]21.[BH4-].[Li+]>O1CCCC1>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[C:16]([CH3:23])=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=4)[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH2:24][OH:25])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57786032Methyl 9-chloro-1-(6-methoxy-2-methylpyridin-3-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate

Product 1

HCID 57785932HCID 57785932, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 9-chloro-1-(6-methoxy-2-methylpyridin-3-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (1.50 g, 3.88 mmol) in tetrahydrofuran (15.0 mL) was added lithium tetrahydroborate (337.8 mg, 15.51 mmol) at 0° C. The reaction mixture was stirred at 50° C. for 6.5 hrs. After cooling, the reaction mixture was quenched with aqueous saturated ammonium chloride at 0° C. The solvent was concentrated and the precipitate was collected by filtration and washed with water to give the title compound as a colorless solid (1.38 g, 3.83 mmol, 99%).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was quenched with aqueous saturated ammonium chloride at 0° C
  3. concentrationThe solvent was concentrated
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-2aedf8ce4bcc45909c333adfbc2f8c50
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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