Lithium borohydride → HCID 57785919, compound

HRID 1399154Notes

Reaction equation

HRID 1399154 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3=[N:14][C:15]4[C:16](=[C:17]([C:22](OC)=[O:23])[CH:18]=[CH:19][C:20]=4[Cl:21])[N:12]3[CH2:11][CH2:10][CH2:9]2)=[C:4]([Cl:26])[CH:3]=1.[BH4-].[Li+]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3=[N:14][C:15]4[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]([CH2:22][OH:23])[C:16]=4[N:12]3[CH2:11][CH2:10][CH2:9]2)=[C:4]([Cl:26])[CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57786131HCID 57786131, compound

Product 1

HCID 57785919HCID 57785919, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 1-(4-bromo-2-chlorophenyl)-9-chloro-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (2.00 g, 4.39 mmol) in tetrahydrofuran (15.0 mL) was added lithium tetrahydroborate (382.8 mg, 17.58 mmol) at 0° C. The reaction mixture was stirred at 40° C. for 15 hrs. The starting material wasn't consumed completely. The reaction mixture was stirred at 50° C. for 4.5 hrs. After cooling, the reaction mixture was quenched with water 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 (1.70 g, 3.97 mmol, 90%).

Workup

  1. customThe starting material wasn't consumed completely
  2. stirringThe reaction mixture was stirred at 50° C. for 4.5 hrs
  3. temperatureAfter cooling
  4. customthe reaction mixture was quenched with water at 0° C
  5. concentrationThe solvent was concentrated
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-dc669dbed83642ff87d1a5a0e34db898
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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