Citric Acid → Benzylsulfamic acid [6-chloro-5-(2-methoxy-phenoxy)-2-methylsulfanyl-pyrimidin-4-yl]-amide

HRID 10259Notes

Reaction equation

Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([S:18][CH3:19])[N:3]=1.[K].[CH2:21]([NH:28][S:29](=[O:32])(=[O:31])[NH2:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O>[Cl:17][C:6]1[N:5]=[C:4]([S:18][CH3:19])[N:3]=[C:2]([NH:30][S:29](=[O:31])(=[O:32])[NH:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

4,6-Dichloro-5-(2-methoxy-phenoxy)-2-methylsulfanyl-pyrimidine (1.5 g) was dissolved in DMSO (30 ml) and benzylsulfamic acid amide potassium salt (2.12 g, Referential Example 22) was added. Stirring was continued for 18 h. The reaction mixture was poured onto water, acidified by solid citric acid (1.9 g), cooled to 0° C. and the precipitate was filtered off and purified by column chromatography over silica gel with hexane/EtOAc=2/1 to give benzylsulfamic acid [6-chloro-5-(2-methoxy-phenoxy)-2-methylsulfanyl-pyrimidin-4-yl]-amide (1.75 g) as a white powder. LC-MS: tR=5.27; [M+H]+=467.04.

Workup

additionThe reaction mixture was poured onto water
filtrationthe precipitate was filtered off
custompurified by column chromatography over silica gel with hexane/EtOAc=2/1

Sources & evidence

ORD record: ord-fbd7d5ace7f143329a76ff9d61c40004
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094781B2

Reaction notes

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