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Potassium Carbonate → HCID 53976813, compound

HRID 454290
Notes
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Reaction equation

HRID 454290 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][CH:17]=[CH:16]4)=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:22][CH3:23].C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:41][C@@H:42]2[O:44][CH2:43]2)(=O)=O)=CC=1>CC(N(C)C)=O>[NH:18]1[C:19]2[C:15](=[CH:14][C:13]([O:12][C:6]3[C:5]4[C:10](=[CH:11][C:2]([O:1][CH2:41][C@H:42]5[CH2:43][O:44]5)=[C:3]([O:22][CH3:23])[CH:4]=4)[N:9]=[CH:8][N:7]=3)=[CH:21][CH:20]=2)[CH:16]=[CH:17]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 154187Glycidyl tosylate, (R)-HCID 1357631167-hydroxy-4-(1H-indol-5-yloxy)-6-methoxyquinazoline

Product 1

HCID 53976813HCID 53976813, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

Nitrogen was bubbled through a mixture of 7-hydroxy-4-(indol-5-yloxy)-6-methoxyquinazoline (3.07 g, 10 mmol), (prepared as described for the starting material in Example 107), potassium carbonate (4.14 g, 30 mmol) and (2R)-(−)-glycidyl tosylate (4.57 g, 20 mmol) in DMA (35 ml) for 5 minutes. The mixture was then stirred at 60° C. for 2 hours under an atmosphere of nitrogen and allowed to cool to ambient temperature. The reaction mixture was filtered and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica by gradient elution with dichloromethane/methanol (100/0 to 95/5), to give (2R)-4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline as a yellow solid (1.92 g, 53%).

Workup

  1. custom(prepared
  2. customfor 5 minutes
  3. temperatureto cool to ambient temperature
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate evaporated in vacuo
  6. customThe residue was purified by column chromatography on silica by gradient elution with dichloromethane/methanol (100/0 to 95/5)

Sources & evidence

ORD record
ord-8cdc97e2f0014ff89f75835a9d8bd8e1
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492560B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes