Ammonia → (5-aminopyridin-3-yl)(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone

HRID 82184Notes

Reaction equation

HRID 82184 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:18]3[C:17](SC)=[N:16][CH:15]=[N:14][C:13]=3[N:12]([CH3:21])[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1.N>[Ni].O1CCOCC1>[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:18]3[CH:17]=[N:16][CH:15]=[N:14][C:13]=3[N:12]([CH3:21])[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 70817471(5-aminopyridin-3-yl)[7-methyl-4-(methylthio)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]methanone

Product 1

HCID 70817432(5-aminopyridin-3-yl)(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanoneYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

Raney nickel (10 g) was added to (5-aminopyridin-3-yl)[7-methyl-4-(methylthio)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]methanone (1.5 g, 5.0 mmol) and conc ammonia (150 mL) in 1,4 dioxane (150 mL). The mixture was refluxed for 6 hours then filtered. The filtrate was evaporated in vacuo and purified by prep HPLC (method 4) to afford the title compound as a brown solid in 100% yield, 1.9 g.

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. filtrationthen filtered
  3. customThe filtrate was evaporated in vacuo
  4. custompurified by prep HPLC (method 4)

Sources & evidence

ORD record
ord-e4999192e9ca4fcbbb6c326ed98f8f49
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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