HCID 69062677, compound → HCID 11283332, compound

HRID 1785451Notes

Reaction equation

HRID 1785451 reaction equation
[CH3:1][CH:2]([NH:16][C:17]1[N:22]=[C:21]([N:23]2[CH2:28][CH2:27][C:26](=[O:29])[N:25]3[CH2:30][CH:31]=[C:32]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:33]=[C:24]23)[CH:20]=[CH:19][N:18]=1)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([N+:13]([O-])=O)[CH3:12])=[CH:6][CH:5]=1>[Pd].CO>[NH2:13][CH:11]([CH3:12])[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH:2]([NH:16][C:17]2[N:22]=[C:21]([N:23]3[CH2:28][CH2:27][C:26](=[O:29])[N:25]4[CH2:30][CH:31]=[C:32]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)[N:33]=[C:24]34)[CH:20]=[CH:19][N:18]=2)[CH3:1])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 69062677HCID 69062677, compound

Product 1

HCID 11283332HCID 11283332, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Through a mixture of 1-(2-{1-methyl-2-[4-(2-nitro-propenyl)-phenyl]-ethylamino}-pyrimidin-4-yl)-8-phenyl-1,2,3,6-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (10 mg, 0.02 mmol) and palladium on carbon (cat) in methanol was bubbled hydrogen through a balloon for 17 h. The mixure was filtered through celite, concentrated and chromatographed on silica gel using 0-4% MeOH/CH2Cl2 to afford an off-white solid. M+1=496. 1NMR (CDCl3) d (3H, 1.28 ppm), d (3H, 1.79 ppm), m (1H, 1.86 ppm), m (2H, 2.22 ppm), m (1H, 2.80 ppm), m (1H, 2.94 ppm), m (3H, 3.75 ppm), m (4H, 4.15 ppm), m (1H, 4.30 ppm), s (1H, 6.60 ppm), d (3H, 7.15 ppm), d (2H, 7.22 ppm), m (3H, 7.44 ppm), dd (2H, 7.91 ppm), d (1H, 8.17 ppm).

Workup

  1. customwas bubbled hydrogen through a balloon for 17 h
  2. filtrationThe mixure was filtered through celite,
  3. concentrationconcentrated
  4. customchromatographed on silica gel using 0-4% MeOH/CH2Cl2
  5. customto afford an off-white solid

Sources & evidence

ORD record
ord-18ca248961c84170805d4e3148ba8a0c
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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