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Sodium hydride → N-(2,6-dichloro-5-fluoro-pyrimidin-4-yl)-N-methyl-methanesulfonamide

HRID 415432
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HRID 415432 반응식
[H-].[Na+].[CH3:3][NH:4][S:5]([CH3:8])(=[O:7])=[O:6].[Cl:9][C:10]1[N:15]=[C:14]([Cl:16])[C:13]([F:17])=[C:12](Cl)[N:11]=1>CN(C=O)C.C1COCC1>[Cl:9][C:10]1[N:11]=[C:12]([N:4]([CH3:3])[S:5]([CH3:8])(=[O:7])=[O:6])[C:13]([F:17])=[C:14]([Cl:16])[N:15]=1
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참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 97632N-MethylmethanesulfonamideHCID 133889932,4,6-Trichloro-5-fluoropyrimidine

생성물 1

HCID 86624844N-(2,6-dichloro-5-fluoro-pyrimidin-4-yl)-N-methyl-methanesulfonamide수율 64%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회
HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of NaH (60% in mineral oil, 176 mg, 8.58 mmol) in anhydrous DMF (2 mL), N-methylmethanesulfonamide (436 mg, 4.0 mmol) in DMF (2 ml) was added. This reaction mixture was stirred for 30 min at room temperature and then added dropwise to the solution of 2,4,6-trichloro-5-fluoropyrimidine (804 mg, 4.0 mmol) in THF (30 ml) at 0° C. The reaction mixture was stirred from 0° C. to room temperature overnight. The solvent was evaporated and the residue was purified by silica gel chromatography (by ISCO Combiflash with gradient 0-30% ethyl acetate in Hexane with 1% TEA. A white solid (700 mg) was obtained, yield 64%. NMR (400 MHz, DMSO) 83.38 (s, 3H), 3.31 (s, 3H).

후처리

  1. stirringThe reaction mixture was stirred from 0° C. to room temperature overnight
  2. customThe solvent was evaporated
  3. customthe residue was purified by silica gel chromatography (by ISCO Combiflash with gradient 0-30% ethyl acetate in Hexane with 1% TEA

출처 및 근거

ORD 기록
ord-9715fa285112424ea9b64663547d55bc
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08088784B2

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