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

HRID 1628733Notes

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[CH:18]=[N:19][C:20]([O:24][CH3:25])=[CH: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[CH:18]=[N:19][C:20]([O:24][CH3:25])=[CH:21][C:22]=4[CH3:23])[CH2:14][CH2:15][CH2:16][N:9]3[C:8]=2[C:7]([CH2:26][OH:27])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Lithium borohydride (290 mg, 13.3 mmol) was added to a stirred solution of methyl 9-chloro-1-(6-methoxy-4-methylpyridin-3-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (1.29 g, 3.33 mmol) in tetrahydrofuran (25 mL) at room temperature, and the mixture was stirred at 40° C. for 24 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 diisopropyl ether to give the title compound as a colorless powder (1.19 g, 3.32 mmol, 99%).

Workup

customThe reaction was quenched by aqueous saturated ammonium chloride at 0° C.
extractionthe mixture was extracted with ethyl acetate
washThe combined organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record: ord-8a5cea4e8a254827988a091a25f6156b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785460B2

Reaction notes

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