2-Amino-4,6-dimethoxypyrimidine → Ethoxysulfuron

HRID 36389

Reaction equation

[CH2:1]([O:3][C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[O:6][S:7]([NH:10][C:11](=[O:22])OC1C=CC=CC=1OCC)(=[O:9])=[O:8])[CH3:2].[NH2:27][C:28]1[N:33]=[C:32]([O:34][CH3:35])[CH:31]=[C:30]([O:36][CH3:37])[N:29]=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[O:6][S:7]([NH:10][C:11]([NH:27][C:28]1[N:29]=[C:30]([O:36][CH3:37])[CH:31]=[C:32]([O:34][CH3:35])[N:33]=1)=[O:22])(=[O:8])=[O:9])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

38.1 g of 2-ethoxyphenyl N-(2-ethoxyphenoxysulfonyl)carbamate are dissolved in 500 ml of toluene, 15.5 g of 2-amino-4,6-dimethoxypyrimidine are added at room temperature, and the mixture is heated for 2 hours at 100° C. After cooling to 30° C., the precipitate is filtered off and washed with 100 ml of toluene. 38.8 g of the desired product are obtained with a purity of 98.8%, corresponding to a yield of 96.4% of theory. The melting point for the product is 147°-149° C. 6.5 g of 2-ethoxyphenol are recovered from the mother liquor by distillation.

Workup

temperatureAfter cooling to 30° C.
filtrationthe precipitate is filtered off
washwashed with 100 ml of toluene

Sources & evidence

ORD record: ord-5547d5c076df4daaaab8b4f4db265ac4
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05414084

Linked notes

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