2-Amino-4,6-dimethoxypyrimidine → Amidosulfuron

HRID 36388

Reaction equation

[CH3:1][S:2]([N:5]([S:7]([NH:10][C:11]([NH:13]N(S(C)(=O)=O)C)=[O:12])(=[O:9])=[O:8])[CH3:6])(=[O:4])=[O:3].N[C:21]1[N:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[N:22]=1>ClC1C=CC=CC=1>[CH3:1][S:2]([N:5]([S:7]([NH:10][C:11]([NH:13][C:21]1[N:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[N:22]=1)=[O:12])(=[O:8])=[O:9])[CH3:6])(=[O:3])=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

32.3 g of 1-[(N-methylsulfonyl-N-methylamino)-sulfonyl]-3-(N-methylsulfonyl-N-methylamino)urea are slurried in 500 ml of chlorobenzene, 15.5 g of 2-amino-4,6-di-methoxypyrimidine are added at 80° C. with stirring, and the mixture is heated for 3 hours at 80° C. After cooling to 20° C., the precipitate is filtered off and washed with 100 ml of chlorobenzene. 36.4 g of the desired product are obtained with a purity of 98.1%, corresponding to a yield of 96.8% of theory. The melting point for the product is 183°-185° C. 5.1 g of N-methylmethanesulfonamide are recovered from the filtrate by distillation, corresponding to a yield of 92.7% of theory.

Workup

temperatureAfter cooling to 20° C.
filtrationthe precipitate is filtered off
washwashed with 100 ml of chlorobenzene

Sources & evidence

ORD record: ord-06b25bb0346b4fd7a734e7384a16ca50
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05414084

Linked notes

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