4,6-Dichloropyrimidine → N-({3-[(6-chloropyrimidin-4-yl)amino]phenyl}methyl)methanesulfonamide

HRID 576669노트

반응식

HRID 576669 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][NH:6][S:7]([CH3:10])(=[O:9])=[O:8].[Cl:14][C:15]1[CH:20]=[C:19](Cl)[N:18]=[CH:17][N:16]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:14][C:15]1[N:16]=[CH:17][N:18]=[C:19]([NH:1][C:2]2[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=2)[CH2:5][NH:6][S:7]([CH3:10])(=[O:9])=[O:8])[CH:20]=1

참가 물질

5

반응물 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 34174207N-(3-aminobenzyl)methanesulfonamide

생성물 1

HCID 53257231N-({3-[(6-chloropyrimidin-4-yl)amino]phenyl}methyl)methanesulfonamide수율 43.6%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

5.309 g N-(3-Amino-benzyl)-methanesulfonamide (obtained in Step 2, 26.5 mmol) and 4.739 g 4,6-dichloropyrimidine (31.81 mmol) was dissolved in 120 cm3 of isopropyl-alcohol, 6.93 cm3 N,N-diisopropyl-ethylamine (5.140 g, 39.76 mmol) was added and the mixture was refluxed for four days. The reaction mixture was cooled to room temperature and the precipitated compound was filtered off. The light yellow product was washed well with diethyl-ether and air-dried. 3.612 g N-[3-(6-Chloro-pyrimidin-4-ylamino)-benzyl]-methanesulfonamide was obtained in more than 98% purity and in 44% overall yield. For analitical results and compound identification see Table 1. The compound was used as a starting material in the preparation of Example 2-32 and 75.

후처리

  1. temperaturethe mixture was refluxed for four days
  2. filtrationthe precipitated compound was filtered off
  3. washThe light yellow product was washed well with diethyl-ether
  4. customair-dried

출처 및 근거

ORD 기록
ord-d8e4415d5f024744ad28666af3698db6
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040529B2

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