4-Chloro-6-[(4-methoxyphenyl)methoxy]-2-phenylpyrimidine → 4-Methoxy-6-[(4-methoxyphenyl)methoxy]-2-phenylpyrimidine

HRID 1429142Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

NaOCH3 (2.64 g, 0.049 mol) was dissolved in MeOH (180 ml). 4-Chloro-6-(4-methoxybenzyloxy)-2-phenylpyrimidine (3.19 g, 9.78 mmol) was added and the reaction mixture was stirred at 0° C. for 1 h. The mixture was then heated to reflux temperature for 7 h. The solvent was evaporated and the compound was purified by column chromatography (Heptane→Heptane/EtOAc 9/1) to give the title compound, (2 g, 64%), MS (M+H)+323.

Workup

temperatureThe mixture was then heated
temperatureto reflux temperature for 7 h
customThe solvent was evaporated
customthe compound was purified by column chromatography (Heptane→Heptane/EtOAc 9/1)

Sources & evidence

ORD record: ord-b01f020df1154cad80f2a499c9ddcd13
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937080B2

Reaction notes

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