2-(Morpholin-4-yl)pyrimidine-5-carbaldehyde → Methyl 3-{2-[2-(morpholin-4-yl)pyrimidin-5-yl]vinyl}benzoate

HRID 2171662Notes

Reaction equation

HRID 2171662 reaction equation
[Br-].[CH3:2][O:3][C:4]([C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=1)[CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5].CC(C)([O-])C.[K+].[N:38]1([C:44]2[N:49]=[CH:48][C:47]([CH:50]=O)=[CH:46][N:45]=2)[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>CN(C=O)C>[N:38]1([C:44]2[N:45]=[CH:46][C:47]([CH:50]=[CH:9][C:8]3[CH:7]=[C:6]([CH:31]=[CH:30][CH:29]=3)[C:4]([O:3][CH3:2])=[O:5])=[CH:48][N:49]=2)[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1

Participants

5

Reactant 3

HCID 31609782-(Morpholin-4-yl)pyrimidine-5-carbaldehydeHCID 10051285Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 77474329Methyl 3-{2-[2-(morpholin-4-yl)pyrimidin-5-yl]vinyl}benzoateYield 74.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[3-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide (930 mg) was mixed with DMF (6 ml), and potassium tert-butoxide (300 mg) was added thereto at 0° C., followed by stirring for 30 minutes. 2-(Morpholin-4-yl)pyrimidine-5-carboaldehyde (300 mg) was added to the reaction mixture, followed by stirring at 0° C. for 1 hour, and stirring again at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and EtOAc and a saturated aqueous sodium hydrogen carbonate solution were then added thereto. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain methyl 3-{2-[2-(morpholin-4-yl)pyrimidin-5-yl]vinyl}benzoate (377 mg).

Workup

  1. additionwas added
  2. customat 0° C.
  3. stirringby stirring at 0° C. for 1 hour
  4. stirringstirring again at room temperature for 1 hour
  5. concentrationThe reaction mixture was concentrated under reduced pressure, and EtOAc
  6. additiona saturated aqueous sodium hydrogen carbonate solution were then added
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-d4e87dcf34d440febe0a1bc7ad8ba0fc
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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