1,4-Cyclohexadiene → HCID 11385806, compound

HRID 1785448Notes

Reaction equation

HRID 1785448 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([NH:14][C:15]2[N:20]=[C:19]([N:21]3[CH2:26][CH2:25][C:24](=[O:27])[N:23]4[CH2:28][CH:29]=[C:30]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[N:31]=[C:22]34)[CH:18]=[CH:17][N:16]=2)[CH3:13])=[CH:7][CH:6]=1)=[N+]=[N-].C1CC=CCC=1>[Pd].C(OC(=O)C)C>[NH2:1][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([NH:14][C:15]2[N:20]=[C:19]([N:21]3[CH2:26][CH2:25][C:24](=[O:27])[N:23]4[CH2:28][CH:29]=[C:30]([C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)[N:31]=[C:22]34)[CH:18]=[CH:17][N:16]=2)[CH3:13])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 86600376HCID 86600376, compound

Product 1

HCID 11385806HCID 11385806, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 1-{2-[2-(4-azidomethyl-phenyl)-1-methyl-ethylamino]-pyrimidin-4-yl}-8-phenyl-1,2,3,6-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one, 1,4-cyclohexadiene (80 μL, 0.80 mmol) and palladium on carbon (100 mg) in ethylacetate (10 mL) was heated to reflux for 3 h and brought to room temperature. The mixture was filtered through celite and concentrated to afford a white solid. M+1=468. 1NMR (CDCl3) d (3H, 1.22 ppm), m (2H, 2.23 ppm), m (1H, 2.76 ppm), m (1H, 2.98 ppm), s (2H, 3.84 ppm), m (4H, 4.11 ppm), m (1H, 4.31 ppm), d (1H, 4.95 ppm), s (1H, 6.60 ppm), d (2H, 7.21 ppm), d (3H, 7.23 ppm), m (3H, 7.44 ppm), dd (2H, 7.91 ppm), d (1H, 8.18 ppm).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. custombrought to room temperature
  4. filtrationThe mixture was filtered through celite
  5. concentrationconcentrated
  6. customto afford a white solid

Sources & evidence

ORD record
ord-8ac111c1e0264127af1000863e1571da
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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