Dimethylformamide → HCID 69924778、化合物

HRID 1005989ノート

反応式

HRID 1005989 の反応式
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[C:9]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[N:10][C:11]([CH3:14])=[N:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:24]N(C)C=O.CI>>[C:1]([O:5][C:6](=[O:23])[N:7]([CH3:24])[C:8]1[C:9]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[N:10][C:11]([CH3:14])=[N:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 69924378HCID 69924378、化合物

生成物 1

HCID 69924778HCID 69924778、化合物収率 99.5%

実験手順

To a solution of 1.83g (5.80 mmol) (2-methyl-4-o-tolyloxy-pyrimidin-5-yl)-carbamic acid tert.-butyl ester in 25 ml N,N-dimethylformamide 0.35 g (68.7 mmol) sodiumhydride (60% dispersion in mineraloil) was added and the reaction mixture stirred for 1 h. After the addition of 0.65 ml (10.4 mmol) methyl iodide at 0°, the reaction mixture was stirred for 2 hrs. The reaction mixture was poured into 100 ml ice-water and three times extracted with 80 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 40:1) to give 1.90 g (99%) methyl-(2-methyl-4-o-tolyloxy-pyrimidin-5-yl)-carbamic acid tert.-butyl ester as a colorless oil, MS (ISP): 330.4 (M+H)+.

後処理

  1. stirringthe reaction mixture was stirred for 2 hrs
  2. extractionextracted with 80 ml CH2Cl2
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 40:1)

出典と根拠

ORDレコード
ord-5cd46b2602a24a9596a23090c5c82182
出典データセット
uspto-grants-2004_09
特許番号
US06787539B2

反応ノート

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