HCID 57593146, compound → HCID 57593155, compound

HRID 1785422Notes

Reaction equation

HRID 1785422 reaction equation
[N+:1]([C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][N:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:16]=3)[C:7]2=[N:6][C:5]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][N:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:16]=3)[C:7]2=[N:6][C:5]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 1

HCID 57593146HCID 57593146, compound

Product 1

HCID 57593155HCID 57593155, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3-nitro-9-(2-phenethylamino-pyrimidin -4-yl)-2-phenyl -6,7,8,9tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (40 mg, 0.09 mmol) in methanol (10 mL) was stirred with 10 % palladium on carbon (5 mg) under an atmosphere of hydrogen for 4 h. Reaction mixture filtered through a bed of Celite, and final product isolated as a white solid after removal of solvent under vacuum. M+1=440 1NMR (CDCl3) t (2H, 2.20 ppm), t (2H, 2.91 ppm), dd (2H, 3.67 ppm), s (2H, 4.07 ppm), m (4H, 4.15 ppm), s (1H, 5.10 ppm), d (1H, 7.17 ppm), m (3H, 7.24 ppm), m (2H, 7.31 ppm), m (1H, 7.36 ppm), t (2H, 7.46 ppm), d (2H, 7.79 ppm), d (1H, 8.03 ppm).

Workup

  1. customReaction mixture
  2. filtrationfiltered through a bed of Celite, and final product
  3. customisolated as a white solid
  4. customafter removal of solvent under vacuum

Sources & evidence

ORD record
ord-a43844c13103496dbf3e3f66108a136a
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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