Lithium borohydride → HCID 57785948, compound

HRID 1628706Notes

Reaction equation

[BH4-].[Li+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:28](OC)=[O:29])=[C:8]2[C:12]=1[N:11]=[C:10]1[N:13]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F: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[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=4[C:24]([F:26])([F:25])[F:27])[CH2:14][CH2:15][CH2:16][N:9]3[C:8]=2[C:7]([CH2:28][OH:29])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Lithium borohydride (2.14 g, 98.1 mmol) was added to a stirred solution of methyl 9-chloro-1-[4-chloro-2-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (10.9 g, 24.5 mmol) in tetrahydrofuran (80 mL) at room temperature, and the mixture was stirred at room temperature for 12 hr and at 50° C. for 4 hr. The reaction was quenched by methanol, and the mixture was diluted with aqueous saturated ammonium chloride at 0° C. and 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 (8.81 g, 21.2 mmol, 87%).

Workup

customThe reaction was quenched by methanol
additionthe mixture was diluted with aqueous saturated ammonium chloride at 0° C.
extractionextracted 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 ethyl acetate/diisopropyl ether

Sources & evidence

ORD record: ord-0b03128708a842469e0de8df5e3e9b98
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785460B2

Reaction notes

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