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

HRID 1629018
Notes
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Reaction equation

HRID 1629018 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 68771677Methyl 1-(3-chloropropyl)-4-methoxy-2-[(2-methoxy-4,6-dimethylpyrimidin-5-yl)amino]-1H-benzimidazole-7-carboxylate

Product 1

HCID 57785995Methyl 9-methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylateYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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

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

Sources & evidence

ORD record
ord-4ad86af9bd794f9ba7d5b1e9db89b996
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785460B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes