4-(2-(Diethylamino)ethoxy)aniline → 2-[[4-[2-(Diethylamino)ethoxy]phenyl]amino]-4-(methylamino)-5-nitropyrimidine

HRID 1375391Notes

Reaction equation

HRID 1375391 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1.[CH2:13]([N:15]([CH2:26][CH3:27])[CH2:16][CH2:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)[CH3:14]>C1COCC1.CC(O)C>[CH2:26]([N:15]([CH2:13][CH3:14])[CH2:16][CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([NH:23][C:2]2[N:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=2)=[CH:24][CH:25]=1)[CH3:27]

Participants

5

Reactant 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 71472322-chloro-N-methyl-5-nitropyrimidin-4-amine

Product 1

HCID 587867952-[[4-[2-(Diethylamino)ethoxy]phenyl]amino]-4-(methylamino)-5-nitropyrimidineYield 80%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.89 g (10 mmol) of 2-chloro-4-(methylamino)-5-nitropyrimidine in 100 mL THF at −78° C. is added a solution of 2.48 g (12 mmol) of 4-[2-(diethylamino)ethoxy]aniline in 100 mL of 2-propanol, and the resulting mixture is allowed to warm slowly to room temperature. The precipitate is collected, washed with 2-propanol, and dissolved in water. After being filtered through celite, the aqueous solution is basified with aqueous ammonia, and the resulting precipitate is collected, washed with water, and dried, to give 2.88 g (80%) of the title compound: mp (EtOH)163–164° C.

Workup

  1. customThe precipitate is collected
  2. washwashed with 2-propanol
  3. dissolutiondissolved in water
  4. filtrationAfter being filtered through celite
  5. customthe resulting precipitate is collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-228319bfb2be48bd97a0504dc505abe6
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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