Water → Methyl 9-methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate

HRID 1399370Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[C:10]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:12]=[C:13]([O:14][CH3:15])[C:8]=2[N:7]=[C:6]1[NH:20][C:21]1[C:22]([CH3:30])=[N:23][C:24]([O:28][CH3:29])=[N:25][C:26]=1[CH3:27].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:15][O:14][C:13]1[CH:12]=[CH:11][C:10]([C:16]([O:18][CH3:19])=[O:17])=[C:9]2[C:8]=1[N:7]=[C:6]1[N:20]([C:21]3[C:22]([CH3:30])=[N:23][C:24]([O:28][CH3:29])=[N:25][C:26]=3[CH3:27])[CH2:2][CH2:3][CH2:4][N:5]21

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of methyl 1-(3-chloropropyl)-4-methoxy-2-[(2-methoxy-4,6-dimethylpyrimidin-5-yl)amino]-1H-benzimidazole-7-carboxylate (878.9 mg, 2.03 mmol) and potassium carbonate (0.84 g, 6.08 mmol) in N,N-dimethylformamide (9.0 mL) was stirred at 70° C. for 16 hr. Water was added to the reaction mixture at room temperature and the mixture was extracted with ethyl acetate. The organic layer was washed with water (×3) and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The Precipitated pale yellow solid was collected by filtration, washed with diisopropyl ether to give the title compound (720.7 mg, 1.81 mmol, 89%) as a pale yellow solid.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water (×3) and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
filtrationThe Precipitated pale yellow solid was collected by filtration
washwashed with diisopropyl ether

Sources & evidence

ORD record: ord-10360b8e29ec49979f29bc25a962f730
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901141B2

Reaction notes

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