Ammonia → 2-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

HRID 1920040Notes

Reaction equation

HRID 1920040 reaction equation
CN1CCCC1=O.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[NH:18][C:19]1[N:24]=[C:23]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[C:22](C(O)=O)=[CH:21][N:20]=1.N>O>[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[NH:18][C:19]1[N:24]=[C:23]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH:22]=[CH:21][N:20]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 59253663HCID 59253663, compound

Product 1

HCID 106861492-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

To 25 mL N-methylpyrrolidone, 5.0 g 2-[(2-methyl-5-nitrophenyl)amino]-4-(3-pyridinyl)pyrimidine-5-carboxylic acid and 0.2 g cupric oxide is added. The mixture is heated to 180° C. for 2 hours, then cooled to 60° C., and 30% aqueous ammonia 1 mL and 50 mL water is added. It is cooled to 25° C., and the precipitate is filtrated, yielding, upon drying, 4.3 g of product with HPLC purity of 97% (A %), which is identified through GC-MS.

Workup

  1. temperaturecooled to 60° C.
  2. temperatureIt is cooled to 25° C.
  3. filtrationthe precipitate is filtrated
  4. customyielding
  5. customupon drying

Sources & evidence

ORD record
ord-21dd3cf488504ff0887500333ff43ed5
Source dataset
uspto-grants-2012_05
Patent number
US08168787B2

Reaction notes

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