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

Benzyl Bromide → 5-hexynyluracil

HRID 1783598
노트
인쇄 미리보기

반응식

HRID 1783598 반응식
I[C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH:10]#[C:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:24]([C:28]1[O:37][C:31]2[CH:32]=[N:33][C:34](=[O:36])[NH:35][C:30]=2[CH:29]=1)[CH2:25][CH2:26][CH3:27]>CN(C=O)C.[OH-].[K+]>[C:10]([C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1)#[C:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH2:24]([C:28]1[O:37][C:31]2[CH:32]=[N:33][C:34](=[O:36])[NH:35][C:30]=2[CH:29]=1)[CH2:25][CH2:26][CH3:27].[CH2:16]([N:35]1[C:30]2[CH:29]=[C:28]([CH2:24][CH2:25][CH2:26][CH3:27])[O:37][C:31]=2[CH:32]=[N:33][C:34]1=[O:36])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 7498Benzyl BromideHCID 127321-HexyneHCID 696725-IodouracilHCID 69060553HCID 69060553, 화합물

생성물 3

HCID 116799645-hexynyluracilHCID 69060553HCID 69060553, 화합물HCID 69065535HCID 69065535, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 14797Potassium Hydroxide용매

반응 조건

온도
65 °C

실험 절차

As above, 5-hexynyluracil and 6-n-butylfuranopyrimidin-2-one was prepared from 3.0 g of 5-iodouracil and 3.0 mL of 1-hexyne at 50° C. for 24 hours. Triethylamine solvent was completely distilled off at reduced pressure and a pale yellow slurry was obtained. This slurry was dissolved in 50.0 mL of DMF containing 0.70 g of KOH, and the resulting dark red solution was heated in an oil bath at 65° C. for 10 minutes. Then, 3.0 mL of benzylbromide was added to the red solution and the reaction was allowed to proceed under an Ar atmosphere until complete benzylation of 6-n-butylfuranopyrimidin-2-one to yield 1-benzyl-6-n-butylfuranopyrimidin-2-one. This alkylation took approximately 9 hours and it was monitored by TLC, as both 6-n-butylfuranopyrimidin-2-one and 1-benzyl-6-n-butylfuranopyrimidin-2-one are fluorescent under UV light but have significantly different Rf values in various solvent systems including EtOAc MeOH/Hexanes:10/1/4 and EtOAc/Ether:2/1. Once the alkylation was complete, DMF solvent was distilled off under reduced pressure and 50.0 mL of dry acetone was added to the resulting slurry to precipitate potassium bromide that was removed by gravity filtration. The filtrate was evaporated to a dark red viscous oil that was dissolved in 40.0 mL of chloroform and extraction was performed with 5% aqueous solution of EDTA (sodium salt) 2×40.0 mL and then once with 40.0 mL of distilled water.

후처리

  1. distillationTriethylamine solvent was completely distilled off at reduced pressure
  2. customa pale yellow slurry was obtained

출처 및 근거

ORD 기록
ord-8e381f6d16db417595dcaa7f6ee26e2a
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07501429B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트