p-Toluidine → 2,6-Bis(p-tolylamino)-3-nitro-pyrimidine

HRID 598740Notes

Reaction equation

Cl[CH:2]1[N:7]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:5][C:4](Cl)=[N:3]1.[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=1.CC[N:22]([CH:26]([CH3:28])[CH3:27])C(C)C>O1CCOCC1>[C:13]1([CH3:12])[CH:18]=[CH:17][C:16]([NH:19][CH:2]2[N:7]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:5][C:4]([NH:22][C:26]3[CH:27]=[CH:18][C:13]([CH3:14])=[CH:12][CH:28]=3)=[N:3]2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 2,6-dichloro-3-nitropyrimidine (194 mg, 1 mmol), p-tolylamine (236 mg, 2.2 mmol) and DIEA (524 μL, 3 mmol) in 3 mL dioxane was stirred in microwave at 200° C. for 20 min. After removal of the solvent, the residue was dissolved in chloroform and subjected to silica gel column purification to give 319 mg (yield: 95%) title compound. Calculated mass=335. Observed mass=336.

Workup

customAfter removal of the solvent
dissolutionthe residue was dissolved in chloroform
customsubjected to silica gel column purification

Sources & evidence

ORD record: ord-efadfc5c84e842c1aebdd1e58bab0b12
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897599B2

Reaction notes

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