Pyridine → 5-(2-Methylsulfanyl-pyrimidin-4-yl)-thiophene-2-sulfonic acid dimethylamide

HRID 1012169

반응식

HRID 1012169 반응식
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[S:13][C:12]([S:14](Cl)(=[O:16])=[O:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.[N:18]1[CH:23]=CC=C[CH:19]=1.CNC.C1COCC1>C(Cl)Cl>[CH3:19][N:18]([CH3:23])[S:14]([C:12]1[S:13][C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=2)=[CH:10][CH:11]=1)(=[O:16])=[O:15]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 27369955-(2-(Methylthio)-4-pyrimidinyl)-2-thiophenesulfonyl chlorideHCID 22320367Dimethylamine tetrahydrofuran2회

생성물 1

HCID 28204715-(2-Methylsulfanyl-pyrimidin-4-yl)-thiophene-2-sulfonic acid dimethylamide수율 74.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 5-(2-methylsulfanyl-pyrimidin-4-yl)-thiophene-2-sulfonyl chloride (200 mg, 0.652 mmol) in 6 mL DCM was treated with pyridine (0.078 mL, 0.97 mmol) and 2 M dimethylamine/THF (0.485 mL, 0.97 mmol). The solution was stirred overnight. Additional 2 M dimethylamine/THF (0.400 mL, 0.8 mmol) was added and the reaction was stirred overnight. The mixture contained <5% starting material by LCMS. The mixture was washed 2×1 N HCl, 1× brine and dried over Na2SO4. 5-(2-Methylsulfanyl-pyrimidin-4-yl)-thiophene-2-sulfonic acid dimethylamide (154 mg, 74.9%) was obtained as an off-white solid, >95% pure by LCMS. This material was taken to the next step. MS: m/z 316 (M+H+).

후처리

  1. stirringthe reaction was stirred overnight
  2. washThe mixture was washed 2×1 N HCl, 1× brine
  3. dry with materialdried over Na2SO4

출처 및 근거

ORD 기록
ord-d0e4044db25148f8877dee812c165507
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977481B2

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