Citric Acid → n-Propanesulfonic acid [6-[2-(5-methylsulfanyl-pyrimidin-2-yloxy)-ethoxy]-5-(2-methoxy-phenoxy)-[2,2']bipyrimidinyl-4-yl]-amide

HRID 2252732노트

반응식

HRID 2252732 반응식
[OH:1][CH2:2][CH2:3][O:4][C:5]1[N:10]=[C:9]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:8]=[C:7]([NH:17][S:18]([CH2:21][CH2:22][CH3:23])(=[O:20])=[O:19])[C:6]=1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32].[H-].[Na+].Cl[C:36]1[N:41]=[CH:40][C:39]([S:42][CH3:43])=[CH:38][N:37]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:43][S:42][C:39]1[CH:38]=[N:37][C:36]([O:1][CH2:2][CH2:3][O:4][C:5]2[N:10]=[C:9]([C:11]3[N:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[N:8]=[C:7]([NH:17][S:18]([CH2:21][CH2:22][CH3:23])(=[O:20])=[O:19])[C:6]=2[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])=[N:41][CH:40]=1

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 219795322-Chloro-5-(methylthio)pyrimidineHCID 71499649n-Propanesulfonic acid [6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-[2,2']bipyrimidinyl-4-yl]-amide

생성물 1

HCID 59645273n-Propanesulfonic acid [6-[2-(5-methylsulfanyl-pyrimidin-2-yloxy)-ethoxy]-5-(2-methoxy-phenoxy)-[2,2']bipyrimidinyl-4-yl]-amide수율 52.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

n-Propanesulfonic acid [6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-[2,2′]bipyrimidinyl-4-yl]-amide (92 mg) was dissolved in THF (6 ml). Sodium hydride (40 mg) and 2-chloro-5-methylsulfanyl-pyrimidine (71 mg) were added and the mixture was heated to 75° C. for 6 h, then poured onto water, acidified with solid citric acid and the precipitate was filtered off. The crude material was purified by crystallization from methanol to give n-propanesulfonic acid [6-[2-(5-methylsulfanyl-pyrimidin-2-yloxy)-ethoxy]-5-(2-methoxy-phenoxy)-[2,2′]bipyrimidinyl-4-yl]-amide (61 mg) as a white powder. LC-MS: tR: 4.37, [M+H]+: 586.19.

후처리

  1. additionpoured onto water
  2. filtrationthe precipitate was filtered off
  3. customThe crude material was purified by crystallization from methanol

출처 및 근거

ORD 기록
ord-ef94d26068464de0a4bd7dd239b8fcfc
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07323465B2

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