Acetic Anhydride → [2-(N-Methyl-acetamido)-quinazolin-4-yl]-(4-dimethylaminophenyl)-methylamine

HRID 2381011Notes

Reaction equation

[CH3:1][NH:2][C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:40](OC(=O)C)(=[O:42])[CH3:41]>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][N:2]([C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:16]=[CH:17][C:18]([N:21]([CH3:22])[CH3:23])=[CH:19][CH:20]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[C:40](=[O:42])[CH3:41]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2-methylamino-quinazolin-4-yl)-(4-dimethylaminophenyl)-methylamine (40 mg, 0.13 mmol) in 4 mL of methylenechloride cooled at 0° C. was added triethylamine (50 uL, 0.36 mmol), few crystals of dimethylaminopyridine and acetic anhydride (50 uL, 0.53 mmol). The reaction mixture was stirred for 1 h at 0° C., warmed to room temperature, and stirred overnight. The reaction mixture was diluted with 25 mL of ethyl acetate and washed with 25 mL of saturated sodium bicarbonate. The organic layer was dried over anhydrous NaSO4, filtered and concentrated. The residue was purified by chromatography (40% ethyl acetate/hexane) to give the title compound (39 mg, 0.11 mmol, 85%). 1H NMR (CDCl3): 7.65-7.69 (m, 1H), 7.52 (ddd, J=8.4, 6.6, 1.8, 1H), 6.93-7.12 (m, 4H), 6.72 (m, 2H), 3.56 (s, 3H), 3.01 (s, 6H), 2.52 (s, 3H).

Workup

temperaturewarmed to room temperature
stirringstirred overnight
washwashed with 25 mL of saturated sodium bicarbonate
dry with materialThe organic layer was dried over anhydrous NaSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography (40% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-61393c24458e4eb89aab7f3cd39e15e1
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258145B2

Reaction notes

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