HCID 18507480, compound → HCID 18507575, compound

HRID 1356054Notes

Reaction equation

HRID 1356054 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:25])=[CH2:24])=[CH:19][CH:18]=2)[N:3]=1.[H][H]>C(O)C.O1CCOCC1.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4]([NH:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:21][CH:22]=2)[N:3]=1

Participants

6

Reactant 2

HCID 18507480HCID 18507480, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18507575HCID 18507575, compoundYield 1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 200 mg (0.60 mmol) 2-amino-4-furan-2-yl-6-(4-isopropenyl-benzylamino)-pyrimidine-5-carbonitrile in 15 ml ethanol and 15 ml dioxane was stirred with a spatula end of 10% palladium on charcoal under 1 atm of hydrogen for 16 h at room temperature. After filtration to remove the catalyst, the reaction mixture was concentrated in vacuo. HPLC afforded 2 mg (1%) 2-amino-4-furan-2-yl-6-(4-isopropyl-benzylamino)-pyrimidine-5-carbonitrile as a white crystalline solid. ES-MS m/e (%): 334 (M+H+, 100).

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst
  3. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-98419735ea014619980dc2ad0cae4f03
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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