Methyl iodide → [6-(6-methoxy-4-methyl-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-pyridin-3-yl]-carbamic acid tert-butyl ester

HRID 1422927Notes

Reaction equation

HRID 1422927 reaction equation
CI.[C:3]([O:7][C:8](=[O:32])[NH:9][C:10]1[CH:11]=[N:12][C:13]([CH:16]2[NH:29][C:28]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:30][CH3:31])[N:26]=4)[N:21]=[CH:20][C:19]=3[O:18][CH2:17]2)=[CH:14][CH:15]=1)([CH3:6])([CH3:5])[CH3:4].[C:33](=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:3]([O:7][C:8](=[O:32])[NH:9][C:10]1[CH:11]=[N:12][C:13]([CH:16]2[N:29]([CH3:33])[C:28]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:30][CH3:31])[N:26]=4)[N:21]=[CH:20][C:19]=3[O:18][CH2:17]2)=[CH:14][CH:15]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 67247039[6-(6-methoxy-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-pyridin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 67247488[6-(6-methoxy-4-methyl-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-pyridin-3-yl]-carbamic acid tert-butyl esterYield 123.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (10.5 μL, 0.17 mmol, 1.0 eq) is added at room temperature to a stirred solution of [6-(6-methoxy-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-pyridin-3-yl]-carbamic acid tert-butyl ester (70 mg, 0.17 mmol, 1.0 eq) in N,N-dimethylformamide (4 mL), followed by cesium carbonate (55 mg, 0.17 mmol, 1.0 eq). After 4 hours stirring at room temperature, solvent is evaporated and the residue is extracted with dichloromethane (3×10 mL) and water (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford [6-(6-methoxy-4-methyl-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-pyridin-3-yl]-carbamic acid tert-butyl ester as an orange viscous oil (89 mg, 75% yield) that is directly engaged in the next step.

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with dichloromethane (3×10 mL) and water (10 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5c4e37a62673477ab94099f64db5d782
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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