Uracil → 186386-84-5

HRID 342537ノート

反応式

HRID 342537 の反応式
[H-].[Na+].[NH:3]1[CH:10]=[CH:9][C:7](=[O:8])[NH:6][C:4]1=[O:5].[CH3:11][Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][O:15][CH2:16]Cl>CN(C=O)C.O>[CH3:11][Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][O:15][CH2:16][N:3]1[CH:10]=[CH:9][C:7](=[O:8])[NH:6][C:4]1=[O:5]

参加物

6

反応物 3

HCID 1174UracilHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

生成物 1

HCID 15313904186386-84-5収率 14.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A solution of 60% sodium hydride (2 g, 50 mmol) in mineral oil was washed with hexanes (2×20 mL) and cooled to 0° C. The solution was diluted with DMF (200 mL) and then uracil (5.6 g, 50 mmol) was added portionwise over 30 minutes. The mixture was treated with 2-(trimethylsilyl)ethoxymethyl chloride (8.8 mL, 50 mmol) and allowed to warm to 25° C. and stand 4 hours. The reaction mixture was diluted with water (500 mL) and extracted with diethyl ether (4×100 mL). The combined extract was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography on silica gel eluting with hexanes/ethyl acetate (2:1) to give 1-[2-(trimethylsilyl)ethoxymethyl]-2,4(1H,3H)-pyrimidinedione (1.8 g, 7.4 mmol), M.p. 120°-122° C.

後処理

  1. temperatureto warm to 25° C.
  2. extractionextracted with diethyl ether (4×100 mL)
  3. extractionThe combined extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel eluting with hexanes/ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-c4b2b0c0221c410eba4c2eed7db8f5b7
出典データセット
uspto-grants-1999_01
特許番号
US05859014

反応ノート

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