홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Methanesulfonyl chloride → 2-Amino-5-(4-chloromethyl-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-triisopropylbenzenesulfonate

HRID 2207105
노트
인쇄 미리보기

반응식

HRID 2207105 반응식
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16]O)=[CH:12][C:11]=2[O:18][CH3:19])=[C:4]([CH3:20])[N:3]=1.C(N(CC)C(C)C)(C)C.[CH:30]([C:33]1[CH:38]=[C:37]([CH:39]([CH3:41])[CH3:40])[CH:36]=[C:35]([CH:42]([CH3:44])[CH3:43])[C:34]=1[S:45](Cl)(=[O:47])=[O:46])([CH3:32])[CH3:31].[Cl-].[Li+].CS([Cl:55])(=O)=O>O1CCCC1.O>[CH:42]([C:35]1[CH:36]=[C:37]([CH:39]([CH3:40])[CH3:41])[CH:38]=[C:33]([CH:30]([CH3:32])[CH3:31])[C:34]=1[S:45]([O:8][C:6]1[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][Cl:55])=[CH:12][C:11]=2[O:18][CH3:19])=[C:4]([CH3:20])[N:3]=[C:2]([NH2:1])[N:7]=1)(=[O:47])=[O:46])([CH3:43])[CH3:44]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 31297Methanesulfonyl chlorideHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 178492557HCID 178492557, 화합물

생성물 1

HCID 1179927752-Amino-5-(4-chloromethyl-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-triisopropylbenzenesulfonate
수율 66.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-amino-5-(4-hydroxymethyl-2-methoxybenzyl)-6-methylpyrimidin-4-ol (5.0 g) and N,N-diisopropylethylamine (11.7 g) in tetrahydrofuran (50 g), 2,4,6-triisopropylbenzenesulfonyl chloride (8.3 g) was added and refluxed for 10 h. After cooling to RT, lithium chloride (2.3 g) was added to the reaction mixture and stirred for 0.5 h, methanesulfonyl chloride (4.2 g) was added over 0.25 h dropwise and the reaction mixture was stirred for 4 h at RT. To the reaction mixture, water (25 g) was added and extracted with ethyl acetate (25 g). The organic layer was washed with water (25 mL) and concentrated in vacuo. To the residue, toluene (20 g) was added and concentrated on vacuo to obtain a light brown solid. The solid was precipitated with toluene (30 g) to obtain sub-title compound (6.8 g). 1H-NMR (300 MHz, CDCl3) δ 7.17 (2H, s), 6.90-6.82 (3H, m), 5.16 (2H, brs), 4.55 (2H, s), 4.10 (2H, septet, J=6.8 Hz), 3.82 (3H, s), 3.81 (2H, s), 2.91 (1H, septet, J=6.8 Hz), 2.32 (3H, s), 1.25 (6H, d, J=7.2 Hz), 1.19 (12H, d, J=6.8 Hz)

후처리

  1. temperaturerefluxed for 10 h
  2. stirringthe reaction mixture was stirred for 4 h at RT
  3. extractionextracted with ethyl acetate (25 g)
  4. washThe organic layer was washed with water (25 mL)
  5. concentrationconcentrated in vacuo
  6. additionTo the residue, toluene (20 g) was added
  7. concentrationconcentrated on vacuo
  8. customto obtain a light brown solid
  9. customThe solid was precipitated with toluene (30 g)

출처 및 근거

ORD 기록
ord-d2d4a30109c24b33aac73bffec4f2ed0
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09376398B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트