2-Amino-4,6-dimethoxypyrimidine → Methyl 2-[3-(4,6-dimethoxypyrimidin-2-yl)-ureidosulfonyloxy]-3-methoxy-benzoate

HRID 326975Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:5]=1[O:12][S:13]([N:16]=[C:17]=[O:18])(=[O:15])=[O:14].[NH2:20][C:21]1[N:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[N:22]=1>C(Cl)Cl>[CH3:30][O:29][C:23]1[CH:24]=[C:25]([O:27][CH3:28])[N:26]=[C:21]([NH:20][C:17](=[O:18])[NH:16][S:13]([O:12][C:5]2[C:6]([O:10][CH3:11])=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([O:2][CH3:1])=[O:19])(=[O:15])=[O:14])[N:22]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 5.4 g (0.02 mol) of the product from Example 1 in 10 ml of methylene chloride is added dropwise to 3.1 g (0.02 mol) of 2-amino-4,6-dimethoxypyrimidine in 50 ml of methylene chloride at 0° C. The mixture is subsequently stirred at 25° C. for 24 hours and diluted with 50 ml of methylene chloride and the organic phase is washed twice with 50 ml of 2N hydrochloric acid each time and once with 50 ml of water. After drying with sodium sulfate and removing the solvent on a rotary evaporator, an oily product remains, which crystallizes on trituration with diethylether. 6.8 g (77% of theory) of methyl 2-[3-(4,6-dimethoxypyrimidin-2-yl)-ureidosulfonyloxy]-3-methoxy-benzoate of melting point 169°-170° C. are obtained.

Workup

washthe organic phase is washed twice with 50 ml of 2N hydrochloric acid each time
dry with materialAfter drying with sodium sulfate
customremoving the solvent
customon a rotary evaporator
customwhich crystallizes on trituration with diethylether

Sources & evidence

ORD record: ord-f9313004172b46c28d858673f32a89cd
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05272129

Reaction notes

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