N,N-dimethyl-m-phenylenediamine → HCID 68527719, compound

HRID 1988587Notes

Reaction equation

HRID 1988587 reaction equation
CS([C:5]1[N:10]=[C:9]2[N:11]([CH3:26])[C:12](=[O:25])[N:13]([C:15]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=3[CH3:24])[CH2:14][C:8]2=[CH:7][N:6]=1)(=O)=O.[CH3:27][N:28]([CH3:36])[C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=1)[NH2:32]>CO>[CH3:27][N:28]([CH3:36])[C:29]1[CH:30]=[C:31]([NH:32][C:5]2[N:10]=[C:9]3[N:11]([CH3:26])[C:12](=[O:25])[N:13]([C:15]4[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=4[CH3:24])[CH2:14][C:8]3=[CH:7][N:6]=2)[CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 76084N,N-dimethyl-m-phenylenediamineHCID 685260247-methanesulfonyl-1-methyl-3-(2-methyl-5-nitro-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

Product 1

HCID 68527719HCID 68527719, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 7-methanesulfonyl-1-methyl-3-(2-methyl-5-nitro-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (148 mg, 0.39 mmol) and 3-dimethylaminoaniline (530 mg, 3.9 mmol) is stirred for 1 hour at 130° C. The mixture is cooled down to room temperature and suspended in methanol. The precipitate is collected and washed with methanol to give 7-(3-dimethylamino-phenylamino)-1-methyl-3-(2-methyl-5-nitro-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (98 mg, 58%) as a yellow solid.

Workup

  1. temperatureThe mixture is cooled down to room temperature
  2. customThe precipitate is collected
  3. washwashed with methanol

Sources & evidence

ORD record
ord-ee06c94ec7804e1d846b8f9980671742
Source dataset
uspto-grants-2010_01
Patent number
US07642255B2

Reaction notes

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