P-Anisidine → (2-Chloro-5-nitro-pyrimidin-4-yl)-(4-methoxy-phenyl)-amine

HRID 1481245Notes

Reaction equation

HRID 1481245 reaction equation
C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[N:16]=[C:15](Cl)[C:14]([N+:18]([O-:20])=[O:19])=[CH:13][N:12]=1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1>O1CCOCC1>[Cl:10][C:11]1[N:16]=[C:15]([NH:29][C:26]2[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[C:14]([N+:18]([O-:20])=[O:19])=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 89717635(2-Chloro-5-nitro-pyrimidin-4-yl)-(4-methoxy-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.46 g (19.0 mmol) Diisopropylethylamine are added slowly to a solution of 3.36 g (17.3 mmol) 2,4-dichloro-5-nitropyrimidine and 2.13 g (17.3 mmol) p-anisidine in 30 ml dioxane. The mixture is stirred for 3 hours at room temperature. Then it is partitioned between water and dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with ethyl acetate/cyclohexane as eluent giving (2-chloro-5-nitro-pyrimidin-4-yl)-(4-methoxy-phenyl)-amine as orange crystals; HPLC/MS (B): 2.24 min, [M+H] 281;

Workup

  1. customThen it is partitioned between water and dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated
  4. customThe residue is chromatographed on a silica gel column with ethyl acetate/cyclohexane as eluent

Sources & evidence

ORD record
ord-aa3f8427893d485e8d49af7073f2e229
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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