Ammonia → 4-(N-Methylsulfamoyl)phenyl 4-amino-6-chloropyrimidine-5-carboxylate

HRID 1052555Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17](=[O:21])(=[O:20])[NH:18][CH3:19])=[CH:13][CH:12]=2)=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[NH3:23]>O1CCOCC1>[NH2:23][C:6]1[C:7]([C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17](=[O:21])(=[O:20])[NH:18][CH3:19])=[CH:13][CH:12]=2)=[O:9])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-(N-methylsulfamoyl)phenyl 4,6-dichloropyrimidine-5-carboxylate (1.4 g, 3.18 mmol) was dissolved in dioxane (16 ml) and cooled in an ice bath. Ammonia (2.27 ml, 7N in MeOH) was dropwise added and the mixture was stirred at 0° C. for 6 h. The solvent was removed and ethyl acetate added. The solid precipitate was filtered and washed with ethyl acetate to give 750 mg (69% yield) of the title compound. Purity 100%

Workup

temperaturecooled in an ice bath
customThe solvent was removed
additionethyl acetate added
filtrationThe solid precipitate was filtered
washwashed with ethyl acetate

Sources & evidence

ORD record: ord-d30150b697d4411185147de5d2c46150
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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