Hydrochloric Acid → {9-Chloro-1-[6-methoxy-2-(trifluoromethyl)pyridin-3-yl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl}methanol

HRID 1629011Notes

Reaction equation

[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:32](OC)=[O:33])=[C:11]2[C:15]=1[N:14]=[C:13]1[N:16]([C:20]3[C:21]([C:28]([F:31])([F:30])[F:29])=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH2:17][CH2:18][CH2:19][N:12]21.Cl.[Cl-].[NH4+]>C(O)C.O1CCCC1>[Cl:6][C:7]1[C:15]2[N:14]=[C:13]3[N:16]([C:20]4[C:21]([C:28]([F:30])([F:29])[F:31])=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=4)[CH2:17][CH2:18][CH2:19][N:12]3[C:11]=2[C:10]([CH2:32][OH:33])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of calcium chloride (670 mg, 6.04 mmol) in ethanol (15 mL) was added sodium tetrahydroborate (457 mg, 12.08 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hr. A solution of methyl 9-chloro-1-[6-methoxy-2-(trifluoromethyl)pyridin-3-yl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (1.33 g, 3.02 mmol) in tetrahydrofuran (15 mL) was added dropwise to the mixture at 0° C. The mixture was stirred at 0° C. for 12 hr. 1N HCl (ca. 9.0 mL) was added to the reaction mixture at 0° C., and the aqueous ammonium chloride was added to the mixture. The solvent was removed in vacuo. The precipitated solid was collected by filtration, washed with water and diisopropyl ether to give the title compound (1.33 g, 3.02 mmol, quant) as a white solid.

Workup

stirringThe mixture was stirred at 0° C. for 12 hr
customThe solvent was removed in vacuo
filtrationThe precipitated solid was collected by filtration
washwashed with water and diisopropyl ether

Sources & evidence

ORD record: ord-b112e0beb3df40afb49cfa73838d26b5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785460B2

Reaction notes

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