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Acetic Acid → N-(2-{[4-(2,4-dichlorophenyl)-5-(morpholin-4-ylmethyl)pyrimidin-2-yl]amino)ethyl)(tert-butoxy)carboxamide

HRID 31860
ノート
印刷プレビュー

反応式

HRID 31860 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14](C=O)=[CH:13][N:12]=[C:11]([NH:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:10]=1.[C:28]([BH3-])#[N:29].[Na+].C(O)(=O)C.O.[CH2:37]1[CH2:41][O:40][CH2:39][CH2:38]1>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH2:28][N:29]2[CH2:37][CH2:41][O:40][CH2:39][CH2:38]2)=[CH:13][N:12]=[C:11]([NH:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[N:10]=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

6

反応物 5

HCID 176Acetic AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 22142985n-(2-{[4-(2,4-Dichlorophenyl)-5-formylpyrimidin-2-yl]amino}ethyl)(tert-butoxy)-carboxamide

生成物 1

HCID 22142523N-(2-{[4-(2,4-dichlorophenyl)-5-(morpholin-4-ylmethyl)pyrimidin-2-yl]amino)ethyl)(tert-butoxy)carboxamide

反応条件

温度
70 °C

実験手順

N-(2-{[4-(2,4-dichlorophenyl)-5-formylpyrimidin-2-yl]amino}ethyl)(tert-butoxy)-carboxamide (50 mg, 0.121 mmol) was dissolved in 5 mL of THF, 242 μL of sodium cyanoborohydride (1M in THF) and 5 μL of glacial acetic acid added and the mixture was heated to 70° C. for 18 h. Following slow addition of 1 mL of water to decompose excess reagent, the mixture was partitioned between ethyl acetate and saturated citric acid solution. The organic layer was discarded, and aqueous layer was carefully basified with sodium hydoxide to PH 9, then extracted with ethyl acetate twice. The combined organic layers was dried (sodium sulfate), concentrated, and purified by chromatography (selica gel, 10% methanol/methylene chloride) to afford N-(2-{[4-(2,4-dichlorophenyl)-5-(morpholin-4-ylmethyl)pyrimidin-2-yl]amino}ethyl)(tert-butoxy)carboxamide, 30 mg (52%).

後処理

  1. customthe mixture was partitioned between ethyl acetate and saturated citric acid solution
  2. extractionextracted with ethyl acetate twice
  3. dry with materialThe combined organic layers was dried (sodium sulfate)
  4. concentrationconcentrated
  5. custompurified by chromatography (selica gel, 10% methanol/methylene chloride)

出典と根拠

ORDレコード
ord-8cb88e52354f4b3ea0d7f9bc8b783569
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07425557B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート