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Diisopropylethylamine → N-{2-chloro-5-fluoro-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin-4-yl}-N-methylmethanesulfonamide

HRID 415433
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HRID 415433 반응식
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([F:14])=[C:4](Cl)[N:3]=1.[CH3:16][C:17]1[NH:21][N:20]=[C:19]([NH2:22])[CH:18]=1.CCN(C(C)C)C(C)C>CCCCO>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([F:14])=[C:4]([NH:22][C:19]2[CH:18]=[C:17]([CH3:16])[NH:21][N:20]=2)[N:3]=1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 86624844N-(2,6-dichloro-5-fluoro-pyrimidin-4-yl)-N-methyl-methanesulfonamide

생성물 1

HCID 86624842N-{2-chloro-5-fluoro-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin-4-yl}-N-methylmethanesulfonamide수율 95%

시약·촉매·용매 1

HCID 2631-Butanol용매

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온도
50 °C

실험 절차

To a solution of N-(2,6-dichloro-5-fluoropyrimidin-4-yl)-N-methylmethanesulfonamide (Method 31, 914 mg, 3.35 mmol) in n-BuOH (3 ml) was added 5-methyl-1H-pyrazol-3-amine (351 mg, 3.62 mmol, 97% purity) and DIPEA (1.2 ml, 6.9 mmol). The mixture was heated at 50° C. overnight. LC/MS showed the completion of the reaction. The solvent was evaporated and the residue was purified by silica gel chromatography (by ISCO Combiflash with gradient 0-5% methanol in DCM with 1% NH4OH) to afford the title compound as a light yellow solid (1.06 g, 95%). LC-MS, 335 (M+1). NMR (DMSO-d6, 400 MHz) δ12.27 (s, 1H), 10.53 (s, 1H), 6.32 (s, 1H), 3.27 (s, 3H), 3.20 (s, 3H), 2.25 (s, 3H).

후처리

  1. customthe completion of the reaction
  2. customThe solvent was evaporated
  3. customthe residue was purified by silica gel chromatography (by ISCO Combiflash with gradient 0-5% methanol in DCM with 1% NH4OH)

출처 및 근거

ORD 기록
ord-f4dec7189bb04bbf88f0d922c070011a
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08088784B2

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