Water → N4-(4-methoxy-phenyl)-5-nitro-N2-(1-phenyl-1H-pyrazol-4-yl)-pyrimidine-2,4-diamine

HRID 1481246Notes

Reaction equation

HRID 1481246 reaction equation
C(N(C(C)C)CC)(C)C.Cl[C:11]1[N:16]=[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:14]([N+:26]([O-:28])=[O:27])=[CH:13][N:12]=1.[C:29]1([N:35]2[CH:39]=[C:38]([NH2:40])[CH:37]=[N:36]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O>O1CCOCC1>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15]2[C:14]([N+:26]([O-:28])=[O:27])=[CH:13][N:12]=[C:11]([NH:40][C:38]3[CH:37]=[N:36][N:35]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:39]=3)[N:16]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1210211-Phenyl-1H-pyrazol-4-amineHCID 89717635(2-Chloro-5-nitro-pyrimidin-4-yl)-(4-methoxy-phenyl)-amine

Product 1

HCID 89720564N4-(4-methoxy-phenyl)-5-nitro-N2-(1-phenyl-1H-pyrazol-4-yl)-pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

284 g (19.0 mmol) Diisopropylethylamine are added to a solution of 561 mg (2.00 mmol) (2-chloro-5-nitro-pyrimidin-4-yl)-(4-methoxy-phenyl)-amine and 350 mg (2.00 mmol) 1-phenyl-1H-pyrazol-4-ylamine in 6 ml dioxane. The mixture is stirred for 16 hours at room temperature. Then water is added to the reaction mixture, the resulting precipitate is filtered off, washed with water and dried under vacuum giving N4-(4-methoxy-phenyl)-5-nitro-N2-(1-phenyl-1H-pyrazol-4-yl)-pyrimidine-2,4-diamine as yellow crystals; HPLC/MS (B): 2.50 min, [M+H] 404.

Workup

  1. filtrationthe resulting precipitate is filtered off
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-f6427ea721d84cc7a99dcba602d8c388
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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