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Hydrochloric Acid → Methyl alpha-[4-(3-tert.butylphenoxy)-6-dimethylamino-pyrimidin-5-yl]-beta-methoxyacrylate

HRID 1957167
ノート
印刷プレビュー

反応式

HRID 1957167 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][CH:25]=1)[O:8][C:9]1[C:14]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:13]([N:20]([CH3:22])[CH3:21])[N:12]=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl.[C:29](=[O:32])(O)[O-].[Na+].S(OC)(O[CH3:38])(=O)=O>COCCOC.C(OC)=O.[Cl-].[Na+].O.CCCCCC.C(OCC)(=O)C.CCOCC>[C:1]([C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][CH:25]=1)[O:8][C:9]1[C:14]([C:15](=[CH:38][O:32][CH3:29])[C:16]([O:18][CH3:19])=[O:17])=[C:13]([N:20]([CH3:22])[CH3:21])[N:12]=[CH:11][N:10]=1)([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

11

反応物 5

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 19069025Methyl 4-(3-tert.butylphenoxy)-6-dimethylamino-pyrimidin-5-yl-acetate

生成物 1

HCID 67742283Methyl alpha-[4-(3-tert.butylphenoxy)-6-dimethylamino-pyrimidin-5-yl]-beta-methoxyacrylate

試薬・触媒・溶媒 5

HCID 3283Diethyl Ether溶媒HCID 7865Methyl formate溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 21226206Ethyl acetate hexane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

Methyl 4-(3-tert.butylphenoxy)-6-dimethylamino-pyrimidin-5-yl-acetate (10.0 g, 29 mmol) is dissolved in a mixture of 1,2-dimethoxyethane (60 ml) and methyl formate (20 ml). Sodium hydride (1.7 g, 80% in oil, 58 mmol) is added in one portion, the temperature being kept at room temperature. After 5 hours the reaction mixture is carefully acidified with hydrochloric acid. After stirring for 1 hour at +5° C. the mixture is neutralized with solid sodium bicarbonat. The intermediate product is extracted with ether and worked up in the usual way. The resulting oil is stirred in dimethylformamide (20 ml) and dimethyl sulfate (4.7 ml, 50 mmol) for 2 hours at room temperature. Dilution with ether washing with brine and chromatography on silicagel (eluant:hexane/ethyl acetate 1:1) gives the methyl α-[4-(3-tert.butylphenoxy)-6-dimethylamino-pyrimidin-5-yl]-β-methoxyacrylate as a single isomer (5.5 g).

後処理

  1. custombeing kept at room temperature
  2. extractionThe intermediate product is extracted with ether
  3. stirringThe resulting oil is stirred in dimethylformamide (20 ml)

出典と根拠

ORDレコード
ord-674935cd3e5a408eb6377b792fc1ae70
出典データセット
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05783580

反応ノート

読み込み中…

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