Triethylamine → HCID 12904739, compound

HRID 1679904Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:18]([NH2:19])=[N:17][C:12]2[N:13]=[CH:14][N:15]=[CH:16][C:11]=2[CH:10]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].[CH2:25](N(CC)CC)C>ClCCCl>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:18]([NH:19][S:21]([CH3:20])(=[O:23])=[O:22])=[N:17][C:12]2[N:13]=[C:14]([CH3:25])[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred suspension of 3.0 g of 6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-amine in 100 ml of dry 1,2-dichloroethane is cooled to 0° C. and treated with 1.2 g of methanesulfonyl chloride followed by dropwise addition of 1.0 g of triethylamine. Stirring is continued while the mixture is allowed to warm to room temperature during 4 hours. If the reaction is not complete as judged by thin layer chromatography on silica gel, the reaction mixture is cooled to 0° C. and treated with an additional 1.2 g of methanesulfonyl chloride followed by 1.0 g of triethylamine. The mixture is stirred overnight at room temperature, filtered from insoluble material and chromatographed on 150 g of silica gel to separate the crude product. Recrystallization from toluene gives pure N-[6-(2,6-dichlorophenyl)-2-methylpyrido[2,3-d]pyrimidin-7-yl]methanesulfonamide, mp 212°-213° C.

Workup

temperatureto warm to room temperature during 4 hours
temperaturethe reaction mixture is cooled to 0° C.
stirringThe mixture is stirred overnight at room temperature
filtrationfiltered from insoluble material
customchromatographed on 150 g of silica gel
customto separate the crude product
customRecrystallization from toluene

Sources & evidence

ORD record: ord-ffa453e803854075a3b2ecc37f6301c1
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04271164

Reaction notes

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