Methanol → HCID 86710180, compound

HRID 2284414Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[N:11]=[CH:10][C:9]([C:12]3[O:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=3)=[CH:8][C:6]=2[N:7]=1.[CH3:25][OH:26].[C-]#N.[Na+]>C(OCC)(=O)C.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[N:11]=[CH:10][C:9]([C:12]3[O:16][C:15]([C:17]([O:26][CH3:25])=[O:18])=[CH:14][CH:13]=3)=[CH:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 100 mL flask, 5-(2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-7-yl)furan-2-carbaldehyde (0.38 g, 0.0011 mol) and methanol (30 mL) were added and the solution cooled to 0° C. To the reaction mixture, manganese (IV) oxide (0.191 g, 0.0022 mol) and sodium cyanide (0.109 g, 0.0022 mol) were added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and was evaporated under reduced pressure to provide methyl 5-(2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-7-yl)furan-2-carboxylate as a solid (0.35 g). 1H NMR (300 MHz, DMSO-d6): δ 9.19 (d, J=2.1 Hz, 1H), 8.29 (d, J=2.1 Hz, 1H), 7.62 (d, J=3.6 Hz, 1H), 7.54 (d, J=3.6 Hz, 1H), 4.84-4.10 (br s, 4H), 3.87 (s, 3H), 3.81 (t, J=4.8 Hz, 4H): LC-MS (ESI): Calculated mass: 374.0; Observed mass [M+H]+: 375.0 (RT=1.51 min).

Workup

washThe organic layer was washed with water, brine
dry with materialdried over anhydrous sodium sulfate
customwas evaporated under reduced pressure

Sources & evidence

ORD record: ord-ac6155f7c20b4dcfb80a24c17a9e29dc
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145411B2

Reaction notes

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