Citric Acid → (5-Aminopyridin-3-yl){7-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone

HRID 82155Notes

Reaction equation

HRID 82155 reaction equation
C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[Si:14]([O:21][CH2:22][C@@H:23]([N:25]1[C:29]2[N:30]=[CH:31][N:32]=[CH:33][C:28]=2[C:27]([C:34]([C:36]2[CH:37]=[N:38][CH:39]=[C:40]([N:42]=C(C3C=CC=CC=3)C3C=CC=CC=3)[CH:41]=2)=[O:35])=[CH:26]1)[CH3:24])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].O.[OH-].[Na+]>C1COCC1>[NH2:42][C:40]1[CH:41]=[C:36]([C:34]([C:27]2[C:28]3[CH:33]=[N:32][CH:31]=[N:30][C:29]=3[N:25]([C@@H:23]([CH3:24])[CH2:22][O:21][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16])[CH:26]=2)=[O:35])[CH:37]=[N:38][CH:39]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86672079{7-[(1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}{5-[(diphenylmethylene)amino]pyridin-3-yl}methanone

Product 1

HCID 70817668(5-Aminopyridin-3-yl){7-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous citric acid (120 mL, 2.0 M) was added to {7-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}{5-[(diphenylmethylene)amino]pyridin-3-yl}methanone (63.2 g, 110 mmol) (see Preparation 24) in THF (274 mL) and the mixture was stirred at room temperature for 17 hours. The mixture was cooled to 0°, water (200 mL) added and the mixture was basified using sodium hydroxide (28 g). The mixture was extracted with ethyl acetate (150 mL) then the aqueous phase was extracted with ethyl acetate (2×200 mL). The combined organic phases were washed with brine (600 mL), dried over sodium sulfate and evaporated in vacuo to afford the title compound as a semi-solid in quantitative yield, 45.2 g.

Workup

  1. temperatureThe mixture was cooled to 0°
  2. extractionThe mixture was extracted with ethyl acetate (150 mL)
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×200 mL)
  4. washThe combined organic phases were washed with brine (600 mL)
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-92474897b95c43c586ccc3fe22150c99
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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