Dimethylformamide → 3-(5-amino-2-methyl-phenyl)-7-(3-dimethylamino-phenylamino)-1-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 2222243Notes

Reaction equation

HRID 2222243 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[N:15]=[C:14]3[N:16]([CH3:31])[C:17](=[O:30])[N:18]([C:20]4[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][C:21]=4[CH3:29])[CH2:19][C:13]3=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.CN(C=O)C>[Pd].CO>[NH2:26][C:24]1[CH:23]=[CH:22][C:21]([CH3:29])=[C:20]([N:18]2[CH2:19][C:13]3[C:14](=[N:15][C:10]([NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:1])[CH3:32])[CH:4]=4)=[N:11][CH:12]=3)[N:16]([CH3:31])[C:17]2=[O:30])[CH:25]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 68527719HCID 68527719, compound

Product 1

HCID 685247583-(5-amino-2-methyl-phenyl)-7-(3-dimethylamino-phenylamino)-1-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneYield 82.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7-(3-dimethylamino-phenylamino)-1-methyl-3-(2-methyl-5-nitro-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (80 mg, 0.18 mmol) in the mixed solvent of DMF (3 ml) and methanol (3 mL) is added 10% Pd/C, and the reaction mixture was stirred for 12 hours at room temperature under a hydrogen balloon. The reaction mixture is filtered and the filtrate is concentrated in vacuo to give 3-(5-amino-2-methyl-phenyl)-7-(3-dimethylamino-phenylamino)-1-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (60 mg, 81%) as a dark yellow solid.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-423c3d7cba4a4377b96ed465c19e1a95
Source dataset
uspto-grants-2008_05
Patent number
US07371750B2

Reaction notes

Loading…