2-Methyl-6-nitroaniline → HCID 86713581, compound

HRID 2274200Notes

Reaction equation

HRID 2274200 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[N:13]1[CH2:22][C:21]2[C:16](=[N:17][C:18](S(C)(=O)=O)=[N:19][CH:20]=2)[N:15]([CH3:27])[C:14]1=[O:28].[CH3:29][C:30]1[CH:36]=[CH:35][CH:34]=[C:33]([N+:37]([O-:39])=[O:38])[C:31]=1[NH2:32].C([O-])(C)(C)C.[K+]>CN(C)C=O>[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[N:13]1[CH2:22][C:21]2[C:16](=[N:17][C:18]([NH:32][C:31]3[C:33]([N+:37]([O-:39])=[O:38])=[CH:34][CH:35]=[CH:36][C:30]=3[CH3:29])=[N:19][CH:20]=2)[N:15]([CH3:27])[C:14]1=[O:28]

Participants

5

Reactant 3

HCID 112982-Methyl-6-nitroanilineHCID 23665647Potassium tert-butoxideHCID 86713579HCID 86713579, compound

Product 1

HCID 86713581HCID 86713581, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methyl-7-(methylsulfonyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (450 mg, 1.01 mmol) and 2-methyl-6-nitroaniline (230 mg, 1.51 mmol) in 5 mL of N,N-dimethylformamide was added potassium tert-butanolate (339 mg, 3.02 mmol) at RT and stirred for 0.5 h. LCMS showed the reaction was completed. The mixture was quenched by 80 mL of water, and the precipitate was collected via the filtration and dried to give the title compound (290 mg, 56%) as a yellow solid, which was directly used in the next step without further purification. MS (ES+) C22H20Cl2N6O5 requires: 518, 520. Found: 519, 521 [M+H]+.

Workup

  1. customThe mixture was quenched by 80 mL of water
  2. filtrationthe precipitate was collected via the filtration
  3. customdried

Sources & evidence

ORD record
ord-69ca7e2368a84ea1b80fd937cc3972ed
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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