2-Amino-4,6-dimethoxypyrimidine → Ethoxysulfuron

HRID 1030007Notes

Reaction equation

HRID 1030007 reaction equation
[CH2:1]([O:3][C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[O:6][S:7]([N:10]=[C:11]=[O:12])(=[O:9])=[O:8])[CH3:2].[NH2:17][C:18]1[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[N:19]=1>ClCCl>[CH3:27][O:26][C:20]1[CH:21]=[C:22]([O:24][CH3:25])[N:23]=[C:18]([NH:17][C:11](=[O:12])[NH:10][S:7]([O:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[O:3][CH2:1][CH3:2])(=[O:9])=[O:8])[N:19]=1

Participants

4

Reactant 2

HCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 190299582-Ethoxyphenoxysulfonyl isocyanate

Product 1

HCID 3623881EthoxysulfuronYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 97.2 g (0.4 mol) of the product of Example 1 in 100 ml of dichloromethane is added dropwise at 25° C. to 62.0 g (0.4 mol) of 2-amino-4,6-dimethoxypyrimidine in 600 ml of dichloromethane. Stirring at room temperature is continued for 16 hours, the mixture is diluted with 600 ml of dichloromethane, and the organic phase is washed twice with 500 ml portions of 2N hydrochloric acid and once with 500 ml of water. After the mixture has been dried using sodium sulfate and after the solvent has been removed on a rotary evaporator, an oily product remains which crystallizes on trituration with diethyl ether. 145.0 g (91% of theory) of 3-(4,6-dimethoxypyrimidin-2-yl)-1-(2-ethoxyphenoxysulfonyl)urea of melting point 145°-147° C. are obtained.

Workup

  1. washthe organic phase is washed twice with 500 ml portions of 2N hydrochloric acid and once with 500 ml of water
  2. customAfter the mixture has been dried
  3. customafter the solvent has been removed on a rotary evaporator
  4. customcrystallizes on trituration with diethyl ether

Sources & evidence

ORD record
ord-71216268f7ae429fa7aaf10033747492
Source dataset
uspto-grants-1992_04
Patent number
US05104443

Reaction notes

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