N,N-Dimethylaniline → Methyl [4-chloro-6-methyl-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate

HRID 1159674

反応式

HRID 1159674 の反応式
O[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:13])[N:5]=[C:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[N:3]=1.CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:35]>>[Cl:35][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:13])[N:5]=[C:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[N:3]=1

参加物

4

反応物 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178499502HCID 178499502、化合物

生成物 1

HCID 59514487Methyl [4-chloro-6-methyl-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate収率 32.2%

実験手順

A solution of methyl [4-hydroxy-6-methyl-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (1.59 g, 5.0 mmol) and N,N-dimethylaniline (0.56 mL, 4.4 mmol) in POCl3 (2.33 mL, 25 mmol) was refluxed for 14 hours. After cooling to room temperature, the reaction mixture was poured into ice-cold saturated K2CO3. The resulting aqueous layer was extracted with EtOAc and the combined organic extracts was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product thus obtained was chromatographed over silica gel eluting with 20% EtOAc in n-hexane to afford methyl [4-chloro-6-methyl-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (0.54 g, 32% yield) as a white powder.

後処理

  1. additionthe reaction mixture was poured into ice-cold saturated K2CO3
  2. extractionThe resulting aqueous layer was extracted with EtOAc
  3. washthe combined organic extracts was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product thus obtained
  8. customwas chromatographed over silica gel eluting with 20% EtOAc in n-hexane

出典と根拠

ORDレコード
ord-2a257eac0af043d3a69762b1048df3dd
出典データセット
uspto-grants-2010_10
特許番号
US07812160B2

関連ノート

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