Methanol → Methyl 5-(2-chloro-4-morpholino-quinazolin-7-yl)furan-2-carboxylate

HRID 517467

Reaction equation

[Cl:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([C:18]3[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=3)=[CH:7][CH:8]=2)[N:3]=1.[C-]#N.[Na+].[CH3:28][OH:29]>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[C:9]2[C:4](=[CH:5][C:6]([C:18]3[O:22][C:21]([C:23]([O:29][CH3:28])=[O:24])=[CH:20][CH:19]=3)=[CH:7][CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 100 mL flask, 5-(2-chloro-4-morpholino-quinazolin-7-yl)furan-2-carbaldehyde (0.6 g, 0.0017 mol) in MeOH (60 mL) was added and cooled to 0° C. To the reaction flask, manganese (IV) oxide (0.74 g, 0.0085 mol) and sodium cyanide (0.429 g, 0.0085 mol) were added at 0° C. The reaction mixture was stirred at 25° C. for 3 h. The reaction mixture was diluted with chloroform and filtered through a pad of Celite® reagent. The filtrate was washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to get the title compound as a solid [0.52 g, 79%]. 1H NMR (300 MHz, CDCl3): δ 8.18 (s, 1H), 7.87-7.86 (m, 2H), 7.29 (d, J=3.6 Hz, 1H), 6.95 (d, J=3.6 Hz, 1H), 3.93 (s, 3H), 3.89 (s, 8H). LC-MS (ESI): Calculated mass: 373.1; Observed mass: 374.1 (RT: 1.57 min).

Workup

filtrationfiltered through a pad of Celite® reagent
washThe filtrate was washed with water, brine
dry with materialdried over anhydrous sodium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-8aa5d8450bd049a088074213efef9ce3
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115092B2

Linked notes

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