Ammonium formate → 1-[4-Amino-2-(methoxymethyl)phenyl]-3-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)pyridin-2(1H)-one

HRID 452231Notes

Reaction equation

HRID 452231 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C:21]1[C:22](=[O:39])[N:23]([C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][C:28]=2[CH2:36][O:37][CH3:38])[CH:24]=[CH:25][CH:26]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:33][C:30]1[CH:31]=[CH:32][C:27]([N:23]2[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][CH2:19][O:18][Si:1]([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:22]2=[O:39])=[C:28]([CH2:36][O:37][CH3:38])[CH:29]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 59410206HCID 59410206, compound

Product 1

HCID 594101791-[4-Amino-2-(methoxymethyl)phenyl]-3-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

25 g (48 mmol) of the compound from Example 39A are dissolved in 500 ml of ethyl acetate and 500 ml of ethanol. 18 g (286 mmol) of ammonium formate and 1 g of palladium on carbon are added, and the mixture is heated at reflux for 45 min. The reaction solution is then allowed to cool and filtered through silica gel. The filtrate is concentrated to dryness under reduced pressure. This gives 25 g (100% of theory) of the desired product.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 45 min
  3. temperatureto cool
  4. filtrationfiltered through silica gel
  5. concentrationThe filtrate is concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-68f82c99a0854607ad51d6c44c3c746c
Source dataset
uspto-grants-2013_07
Patent number
US08487111B2

Reaction notes

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