Methyl iodide → (4-Methylthio-phenyl)-(2-methyl-quinazolin-4-yl)-methylamine

HRID 2381012Notes

Reaction equation

[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([CH3:20])[N:11]=2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:23]I>CN(C=O)C.CCOC(C)=O>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([CH3:20])[N:11]=2)[CH3:23])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (4-methylthio-phenyl)-(2-methyl-quinazolin-4-yl)-amine (263 mg, 0.94 mmol) in DMF (4 ml) at 0° C. was added sodium hydride (56.4 mg, 1.40 mmol, 60% oil dispersion) and followed by methyl iodide (0.09 ml, 1.40 mmol). The mixture was stirred at 0° C. for 1 h, then allowed to warm to room temperature and stirred for another 2 h. The reaction mixture was diluted with EtOAc (15 ml), washed with saturated NaHCO3 aq., brine, dried over Na2SO4, filtered and concentrated by vacuum. The residue was purified by chromatography on silica gel with acetate and hexane (1:2 to 1:1) as eluent, yielding 120 mg of title compound (40.7%). 1H NMR (CDCl3): 7.76 (d, J=9.0 Hz, 1H), 7.54 (t, J=7.5 Hz, 1H), 7.24-7.19 (m, 2H), 7.10-6.97 (m, 4H), 3.59 (s, 3H), 2.74 (s, 3H), 2.48 (s, 3H)

Workup

temperatureto warm to room temperature
stirringstirred for another 2 h
washwashed with saturated NaHCO3 aq., brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated by vacuum
customThe residue was purified by chromatography on silica gel with acetate and hexane (1:2 to 1:1) as eluent

Sources & evidence

ORD record: ord-680a45d5366946a1b0cd9185001409e5
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258145B2

Reaction notes

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