N,N-Dimethylaniline → 2-[[4-[4-(Tert-butoxycarbonyl)piperazin-1-yl]phenyl]-amino]-4-(cyclopentylamino)-5-nitropyrimidine

HRID 1375396Notes

Reaction equation

HRID 1375396 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][N:3]=1.CN(C)C1C=CC=CC=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][N:36]([C:39]2[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>C1COCC1.CC(O)C.C(O)(=O)C.O>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][N:36]([C:39]2[CH:40]=[CH:41][C:42]([NH:45][C:2]3[N:7]=[C:6]([NH:8][CH:9]4[CH2:13][CH2:12][CH2:11][CH2:10]4)[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][N:3]=3)=[CH:43][CH:44]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

8

Reactant 3

HCID 949N,N-DimethylanilineHCID 71472532-chloro-N-cyclopentyl-5-nitropyrimidin-4-amineHCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

Product 1

HCID 587867852-[[4-[4-(Tert-butoxycarbonyl)piperazin-1-yl]phenyl]-amino]-4-(cyclopentylamino)-5-nitropyrimidineYield 94.4%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.73 g (3 mmol) of 2-chloro-4-(cyclopentylamino)-5-nitropyrimidine and 0.49 g (4 mmol) N,N-dimethylaniline in 10 mL THF is added a solution of 0.94 g (3.4 mmol) of 1-(tert-butoxycarbonyl)-4-(4-aminophenyl)-piperazine in 20 mL of 2-propanol, and the resulting mixture is heated under reflux for 2 hours. After cooling and acidification with acetic acid, the mixture is diluted with water to give 1.37 g (94%) of the title compound: mp (MeOH) 194–196° C.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-1980bb5f90eb4eaa9d824068aa3e4ffe
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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