Methanol → 4-Chloro-6-(3,4-dimethoxy-phenyl)-2-methoxy-pyrimidine

HRID 216152Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)[N:5]=[C:4](S(C)(=O)=O)[N:3]=1.[CH3:22][O-:23].[Na+].CO>COCCOC>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)[N:5]=[C:4]([O:23][CH3:22])[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 4-chloro-6-(3,4-dimethoxy-phenyl)-2-methanesulfonyl-pyrimidine [5.05 g, 0.0154 mol, Intermediate (49)] in ethylene glycol dimethyl ether (100 mL) is chilled to 0° C. and added 25 wt % sodium methoxide in MeOH (1.32 mL, 0.0231 mol). After 15 minutes the reaction is allowed to warm to ambient temperature and stirred overnight. The mixture is concentrated to afford 4-chloro-6-(3,4-dimethoxy-phenyl)-2-methoxy-pyrimidine [4.3 g, 100%, Intermediate (50)]

Workup

temperatureto warm to ambient temperature
concentrationThe mixture is concentrated

Sources & evidence

ORD record: ord-bd8e93ebba644cc69b4c2d20511e4ab0
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193183B2

Reaction notes

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