Ammonium formate → HCID 22736345, compound

HRID 51494Notes

Reaction equation

HRID 51494 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[N:17]([CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[NH2:24][C:22]1[C:23]2[C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)=[CH:16][N:17]([CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:18]=2[N:19]=[CH:20][N:21]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22736420HCID 22736420, compound

Product 1

HCID 22736345HCID 22736345, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-(4-benzyloxyphenyl)-7-(tetrahydropyran-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (2.83 g), 10% palladium on carbon (1.41 g), ammonium formate (2.31 g) and ethanol (250 ml) was boiled under reflux under nitrogen with stirring for 1.5 hours. The mixture was cooled to ambient temperature, filtered, then the filtrate cooled and filtered. The filtrate was evaporated to give a solid 4-[4-amino-7-(4-tetrahydropyranyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]phenol.

Workup

  1. temperatureunder reflux under nitrogen
  2. filtrationfiltered
  3. temperaturethe filtrate cooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-ac67701dbc524d57ad1f7d629b75546f
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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