Cyclohexanone → HCID 18507289, compound

HRID 1356028Notes

Reaction equation

HRID 1356028 reaction equation
C(O[C:9](=O)[NH:10][CH2:11][CH2:12][NH:13][C:14]1[C:19]([C:20]#[N:21])=[C:18]([C:22]2[O:23][CH:24]=[CH:25][CH:26]=2)[N:17]=[C:16]([NH2:27])[N:15]=1)C1C=CC=CC=1.[C:29]1(=O)[CH2:34][CH2:33]C[CH2:31][CH2:30]1.[H][H]>O1CCOCC1.C(O)C.[Pd]>[NH2:27][C:16]1[N:15]=[C:14]([NH:13][CH2:12][CH2:11][NH:10][CH:9]2[CH2:33][CH2:34][CH2:29][CH2:30][CH2:31]2)[C:19]([C:20]#[N:21])=[C:18]([C:22]2[O:23][CH:24]=[CH:25][CH:26]=2)[N:17]=1

Participants

7

Reactant 3

HCID 7967CyclohexanoneHCID 69782384HCID 69782384, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18507289HCID 18507289, compoundYield 46.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 200 mg (0.53 mmol) [2-(2-amino-5-cyano-6-furan-2-yl-pyrimidin-4-ylamino)-ethyl]-carbamic acid benzyl ester and 0.055 ml (0.53 mmol) cyclohexanone in 10 ml dioxane and 5 ml ethanol was stirred with a spatula end of 10% palladium on charcoal under 1 atm of hydrogen for 4 h at room temperature. After filtration to remove the catalyst, the reaction mixture was concentrated in vacuo and the residue triturated in ether to afford 80 mg (46%) 2-amino-4-(2-cyclohexylamino-ethylamino)-6-furan-2-yl-pyrimidine-5-carbonitrile as a white crystalline solid. ES-MS m/e (%): 327 (M+H+, 100), 228 ([M+H—C6H11NH2]+, 40).

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customthe residue triturated in ether

Sources & evidence

ORD record
ord-21428b7ec8f04b4c9f3a965bb6edac5c
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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