Water → 6-methyl-N1-(4-phenylpyrimidin-2-yl)benzene-1,3-diamine hydrochloride

HRID 1180102Notes

Reaction equation

HRID 1180102 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9]C(=O)C)[CH:5]=[CH:6][C:7]=1[CH3:8].[Cl:13][C:14]1[N:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:16][N:15]=1.O>CN(C=O)C>[ClH:13].[CH3:8][C:7]1[C:2]([NH:1][C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]=[CH:16][N:15]=2)=[CH:3][C:4]([NH2:9])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 22865N-(3-amino-4-methylphenyl)acetamideHCID 6053562-Chloro-4-phenylpyrimidine

Product 1

HCID 693525616-methyl-N1-(4-phenylpyrimidin-2-yl)benzene-1,3-diamine hydrochlorideYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(3-amino-4-methyl-phenyl)acetamide (5 g, 25 mmol) in DMF (5 ml) was added 2-chloro-4-phenyl-pyrimidine (4 g, 35 mmol) and KI (0.5 g, 3 mmol), which was stirred at 100° C. overnight, cooled to 10° C. and added to H2O (100 mL). The resulting mixture was extracted with CH2Cl2 (2×100 mL), the combined organic layers dried (Na2SO4) and concentrated in vacuo. The residue was dissolved in conc. HCl (10 mL), stirred at 80° C. for 2 h and concentrated in vacuo to yield 6-methyl-N1-(4-phenylpyrimidin-2-yl)benzene-1,3-diamine hydrochloride (4.5 g, 65%). 1H NMR (CDCl3): 7.96 (m, 2H), 7.50-7.47 (m, 1H), 7.47-7.41 (m, 5H), 7.26 (m, 2H), 2.21(s, 3H); MS (ESI) m/e: 277 (M++1)

Workup

  1. temperaturecooled to 10° C.
  2. extractionThe resulting mixture was extracted with CH2Cl2 (2×100 mL)
  3. dry with materialthe combined organic layers dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in conc. HCl (10 mL)
  6. stirringstirred at 80° C. for 2 h
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c54ffca347904181ada6111916c9c2d5
Source dataset
uspto-grants-2007_10
Patent number
US07279576B2

Reaction notes

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