2-Amino-4-chloro-6-methylpyrimidine → Methyl 2-[3-(4-chloro-6-methylpyrimidin-2-yl)-ureidosulfonyloxy]-3-methoxybenzoate

HRID 326976Notes

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]([Cl:27])[CH:24]=[C:23]([CH3:28])[N:22]=1>C(Cl)Cl>[Cl:27][C:25]1[CH:24]=[C:23]([CH3:28])[N:22]=[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:26]=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 2.9 g (0.02 mol) of 2-amino-4-chloro-6-methylpyrimidine 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 water. After drying with sodium sulfate and removing the solvent on a rotary evaporator, an oily product remains, which crystallizes on trituration with diisopropylether. 7.8 g (91% of theory of methyl 2-[3-(4-chloro-6-methylpyrimidin-2-yl)-ureidosulfonyloxy]-3-methoxybenzoate of melting point 140°-143° 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 diisopropylether

Sources & evidence

ORD record: ord-47c771e9b6e5440d89b1866bf650543c
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05272129

Reaction notes

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