Ethanol → 4-Pyrimidinebutanoic acid,2-amino-6-[[3-fluoro-4-(1h-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino]-,ethyl ester

HRID 16461Notes

Reaction equation

HRID 16461 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]4[NH:28][CH:29]=[CH:30][C:23]=34)=[C:17]([F:31])[CH:16]=2)[N:3]=1.S(=O)(=O)(O)O.[CH2:37](O)[CH3:38]>>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:37][CH3:38])=[O:12])[CH:5]=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]4[NH:28][CH:29]=[CH:30][C:23]=34)=[C:17]([F:31])[CH:16]=2)[N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 587333374-(2-amino-6-{[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino}pyrimidin-4-yl)butyric acid

Product 1

HCID 587333944-Pyrimidinebutanoic acid,2-amino-6-[[3-fluoro-4-(1h-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino]-,ethyl ester

Procedure

396 mg (0.86 mmol) of 4-(2-amino-6-{[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino}pyrimidin-4-yl)butyric acid (from example 130) in 20 ml of ethanol are, after addition of 0.10 ml of sulfuric acid, heated under RF for 20 hours. The mixture is concentrated under reduced pressure, dichloromethane and a little methanol are added and the mixture is extracted with sodium bicarbonate solution. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. This gives the title compound.

Workup

  1. temperatureheated under RF for 20 hours
  2. concentrationThe mixture is concentrated under reduced pressure, dichloromethane
  3. additiona little methanol are added
  4. extractionthe mixture is extracted with sodium bicarbonate solution
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-b9d51c09c1574cbd9ae871b911f5ec69
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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