2-Methyl-6-nitroaniline → HCID 86713561, compound

HRID 524029Notes

Reaction equation

HRID 524029 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[C:26](=[O:27])[N:25]([CH3:28])[C:16]2[N:17]=[C:18](S(C)(=O)=O)[N:19]=[CH:20][C:15]=2[CH:14]=1.[CH3:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([N+:36]([O-])=O)[C:31]=1[NH2:39].CC(C)([O-])C.[K+]>CN(C=O)C.CCOC(C)=O>[NH2:36][C:32]1[CH:33]=[CH:34][CH:35]=[C:30]([CH3:29])[C:31]=1[NH:39][C:18]1[N:19]=[CH:20][C:15]2[CH:14]=[C:13]([C:3]3[C:2]([Cl:1])=[C:7]([O:8][CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=3[Cl:12])[C:26](=[O:27])[N:25]([CH3:28])[C:16]=2[N:17]=1

Participants

6

Reactant 3

HCID 112982-Methyl-6-nitroanilineHCID 23665647Potassium tert-butoxideHCID 86713562HCID 86713562, compound

Product 1

HCID 86713561HCID 86713561, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-8-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one (9) (1.0 g, 2.26 mmol) and 2-methyl-6-nitrobenzenamine (684 mg, 4.5 mmol) in DMF (20 mL), potassium tert-butoxide (756 mg, 6.75 mmol) was added at ˜10° C., and the reaction mixture was stirred at room temperature for 5 minutes. The reaction mixture was diluted with EtOAc (150 mL), and the organic phase was separated, washed with water (2×150 mL) and then brine (150 mL), dried over sodium sulfate, filtered, and concentrated. The residue was recrystallizated with EtOAc to give 2-(2-amino-6-methylphenylamino)-6-(2,6-dichloro-3,5-dimethoxyphenyl)-8-methylpyrido[2,3-d]pyrimidin-7(8H)-one (10) (810 mg, yield 70%) as a yellow solid. MS (ES+) C23H19Cl2N5O5 requires: 515, 517. found: 516, 518 [M+H]+.

Workup

  1. additionwas added at ˜10° C.
  2. customthe organic phase was separated
  3. washwashed with water (2×150 mL)
  4. dry with materialbrine (150 mL), dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2689ddac470c4f57a2acb75647188300
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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