Lithium borohydride → [9-Chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol

HRID 1628755Notes

Reaction equation

HRID 1628755 reaction equation
[BH4-].[Li+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:27](OC)=[O:28])=[C:8]2[C:12]=1[N:11]=[C:10]1[N:13]([C:17]3[C:18]([CH3:26])=[N:19][C:20]([O:24][CH3:25])=[N:21][C:22]=3[CH3:23])[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:18]([CH3:26])=[N:19][C:20]([O:24][CH3:25])=[N:21][C:22]=4[CH3:23])[CH2:14][CH2:15][CH2:16][N:9]3[C:8]=2[C:7]([CH2:27][OH:28])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57786073Methyl 9-chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate

Product 1

HCID 57786330[9-Chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Lithium borohydride (1.93 g, 88.4 mmol) was added to a stirred solution of methyl 9-chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (8.87 g, 22.1 mmol) in tetrahydrofuran (100 mL) at room temperature, and the mixture was stirred at 40° C. for 14 hr. The reaction was quenched by methanol, and the mixture was diluted with aqueous saturated ammonium chloride at 0° C. The mixture was extracted with tetrahydrofuran/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 (8.08 g, 21.6 mmol, 98%).

Workup

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

Sources & evidence

ORD record
ord-5c739bbcbec646ea91316792a987f7e5
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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