P-Anisidine → (4-Methoxy-phenyl)-[6-(4-nitro-phenoxy)-pyrimidin-4-yl]-amine

HRID 1993508Notes

Reaction equation

HRID 1993508 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C>CC(O)C>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=3)[N:5]=[CH:4][N:3]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7732P-Anisidine2×HCID 81531DiisopropylethylamineHCID 143638504-Chloro-6-(4-nitrophenoxy)pyrimidine

Product 1

HCID 68535688(4-Methoxy-phenyl)-[6-(4-nitro-phenoxy)-pyrimidin-4-yl]-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chloro-6-(4-nitro-phenoxy)-pyrimidine (1 g, 3.97 mmol), p-anisidine (514 mg, 4.178 mmol), and diisopropylethylamine (0.715 mL, 4.178 mmol) dissolved in 2-propanol (27 mL) are stirred under reflux under Ar. After 16 h, p-anisidine (245 mg, 1.99 mmol) is added and the reaction mixture is stirred for additional 20 h. After cooling the reaction mixture down to rt, compound of Stage 47.2 precipitates as white crystals: M+H=339.1; 1H-NMR (400 MHz, DMSO-d6): 9.49 (s, 1H, NH-pyrimidinyl), 8.25 (s, 1H, pyrimidine), 8.23/7.40/6.90 (d/d/d/, 9.0 Hz, 2H/4H/2H, phenyl-oxolphenyl-OMe), 6.18 (s, 1H, pyrimidinyl), 3.72 (s, 3H, CH3—O); Rf (MeOH/CH2Cl2=1:9): 0.44; HPLC (System 1): 6.15 min.

Workup

  1. temperatureunder reflux under Ar
  2. stirringthe reaction mixture is stirred for additional 20 h
  3. customprecipitates as white crystals
  4. custom6.15 min.

Sources & evidence

ORD record
ord-7d13028957c74b4c94edbc07131f91bb
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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