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Benzyl Bromide → 5-hexynyluracil

HRID 1783598
ノート
印刷プレビュー

反応式

HRID 1783598 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 7498Benzyl BromideHCID 127321-HexyneHCID 696725-IodouracilHCID 69060553HCID 69060553、化合物

生成物 3

HCID 116799645-hexynyluracilHCID 69060553HCID 69060553、化合物HCID 69065535HCID 69065535、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 14797Potassium Hydroxide溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-8e381f6d16db417595dcaa7f6ee26e2a
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07501429B2

反応ノート

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