Cyclohexene → HCID 18186474, compound

HRID 1357526Notes

Reaction equation

HRID 1357526 reaction equation
[NH:1]([C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][N:11]=[C:10]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([OH:31])[CH2:27][N:28]([CH3:30])[CH3:29])=[CH:20][CH:19]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCCCC=1>C(O)C.[Pd]>[NH2:14][C:13]1[C:8]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9][C:10]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([OH:31])[CH2:27][N:28]([CH3:30])[CH3:29])=[CH:20][CH:19]=2)=[N:11][CH:12]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 18186455HCID 18186455, compound

Product 1

HCID 18186474HCID 18186474, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

4-Anilino-2-{4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]anilino}-5-nitropyrimidine (Example 20, 400 mg, 0.90 mmol) was dissolved in ethanol (20 ml). Under an atmosphere of nitrogen, cyclohexene (5 ml) was added followed by 10% palladium-on-carbon (100 mg). The mixture was heated under reflux for 5 hours, and then a further portion of 10% palladium on carbon (100 mg) was added and heating was continued for 18 hours. The catalyst was removed by filtration through diatomaceous earth and the filtrate was concentrated by evaporation. The resulting oil was purified by column chromatography, eluting with 0-10% 2.0M methanolic ammonia in DCM to give the product as a white solid (300 mg, 80%). NMR: 2.15 (s, 6H), 2.3 (m, 2H), 3.8 (m, 3H), 4.3 (s, 2H), 4.7 (s, 1H), 6.8 (d, 2H), 7.0 (t, 1H), 7.3 (t, 2H), 7.5 (d, 2H), 7.6 (s, 1H), 7.8 (d, 2H), 8.1 (s, 1H), 8.4 (s, 1H); MS (MH+): 395.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperatureheating
  4. customThe catalyst was removed by filtration through diatomaceous earth
  5. concentrationthe filtrate was concentrated by evaporation
  6. customThe resulting oil was purified by column chromatography
  7. washeluting with 0-10% 2.0M methanolic ammonia in DCM

Sources & evidence

ORD record
ord-736f2733b82b4c858e2e051803ab8419
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

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