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

HRID 1180103Notes

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]=[CH:18][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:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:17]=[CH:16][N:15]=2)=[CH:3][C:4]([NH2:9])=[CH:5][CH:6]=1

Participants

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-pyrimidine (3.8 g, 33 mmol)-and KI (0.5 g), 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 (3.75 g, 75%). 1H NMR (CDCl3): 8.36 (dd, J=15.2 & 4.8 Hz, 2H), 7.46 (d, J=2.4 Hz, 1H), 6.97 (d, J=8.0 Hz, 1H), 7.26 (s, 1H), 6.67 (t, J=4.8 Hz, 1H), 6.39 (dd, J=8.0, 2.4, Hz, 1H), 2.20 (s, 3H); MS (ESI) m/e: 201 (M++1).

Workup

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

Sources & evidence

ORD record: ord-4c7f5e545b284613bb2c742ddf003089
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279576B2

Reaction notes

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