HCID 9836613, compound → 2-Amino-4-(4-ethyl-benzylamino)-6-furan-2-yl-pyrimidine-5-carbonitrile

HRID 1356043Notes

Reaction equation

HRID 1356043 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]([CH:23]=[CH2:24])=[CH:19][CH:18]=2)[N:3]=1.[H][H]>C(O)C.[Pd]>[NH2:1][C:2]1[N:3]=[C:4]([NH:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH3:24])=[CH:21][CH:22]=2)[C:5]([C:13]#[N:14])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Participants

5

Reactant 2

HCID 9836613HCID 9836613, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 98800622-Amino-4-(4-ethyl-benzylamino)-6-furan-2-yl-pyrimidine-5-carbonitrileYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 50 mF (0.16 mmol) 2-amino-4-furan-2-yl-6-(4-vinyl-benzylamino)-pyrimidine-5-carbonitrile in 10 ml ethanol 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. Chromatography (ethyl acetate) followed by trituration in ether/hexane afforded 12 mg (24%) 2-amino-4-(4-ethyl-benzylamino)-6-furan-2-yl-pyrimidine-5-carbonitrile as a white crystalline solid. ES-MS m/e (%): 320 (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-ad3a67a3068148889a8d2796a9460350
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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