Chloride → 5-Ethyl-1-(3-acetoxypropyloxymethyl)-6-(3,5-dimethylbenzyl)uracil

HRID 1072968

反応式

HRID 1072968 の反応式
[CH2:1]([C:3]1[C:4](=[O:19])[NH:5][C:6](=[O:18])[NH:7][C:8]=1[CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[CH:11]=1)[CH3:2].CC1C=C(C=C(C)C=1)CC1NC(=O)NC(=O)C=1C(C)C.BrC(C(C)C)C(O)=O.BrC(CC)C(O)=O.[C:55]([O:58][CH2:59][CH2:60][CH2:61][O:62][CH2:63]OC(=O)C)(=[O:57])[CH3:56].C[Si](C)(C)N[Si](C)(C)C.Cl[Si](C)(C)C.[Cl-].[Na]>C(#N)C.ClCCl>[CH2:1]([C:3]1[C:4](=[O:19])[NH:5][C:6](=[O:18])[N:7]([CH2:63][O:62][CH2:61][CH2:60][CH2:59][O:58][C:55](=[O:57])[CH3:56])[C:8]=1[CH2:9][C:10]1[CH:11]=[C:12]([CH3:17])[CH:13]=[C:14]([CH3:16])[CH:15]=1)[CH3:2]

参加物

12

反応物 9

HCID 312ChlorideHCID 6397ChlorotrimethylsilaneHCID 66552-Bromobutanoic acidHCID 112682-Bromoisovaleric acidHCID 13838HexamethyldisilazaneHCID 5360545SodiumHCID 106826455-Ethyl-6-(3,5-dimethylbenzyl)uracilHCID 107309016-(3,5-Dimethylbenzyl)-5-isopropyluracilHCID 124808481-Acetoxy-3-acetoxymethoxypropane

生成物 1

HCID 223866115-Ethyl-1-(3-acetoxypropyloxymethyl)-6-(3,5-dimethylbenzyl)uracil収率 87%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
20 °C

実験手順

To a suspension of 5-ethyl-6-(3,5-dimethylbenzyl)uracil (645 mg, 5 mmol) (prepared as described for the preparation of 6-(3,5-dimethylbenzyl)-5-isopropyluracil in the above Example 1-A but in replacing the 2-bromo-3-methylbutanoic acid by the 2-bromobutanoic acid) and 1-acetoxy-3-acetoxymethoxypropane (prepared as described in the above Example 1-B) (950 mg, 5 mmol) in ethanenitrile (25 ml), were added hexamethyldisilazane (810 mg, 5 mmol) and chlorotrimethylsilane (545 mg, 5 mmol). After 10 minutes under stirring at 20° C., it was added dropwise thereto, in 10 minutes, a solution of tinIV chloride (782 mg, 2.4 mmol) in ethanenitrile (7 ml). After 14 h under stirring, it was added to the reaction medium dichloromethane (70 ml) and an aqueous saturated sodium hydrogenocarbonate solution (70 ml). The organic phase was separated by decantation and the aqueous phase was extracted with dichloromethane (3×50 ml). The collected organic phases were washed with saturated sodium hydrogenocarbonate solution (25 ml), with water (25 ml) and with an aqueous saturated sodium chloride solution (25 ml). The organic phase was dried over sodium sulfate, concentrated, and subjected to a flash column chromatography on silica gel (ethyl acetate/petroleum ether 1:1) to give 0.85 g (87%) of 5-ethyl-1-(3-acetoxypropyloxymethyl)-6-(3,5-dimethylbenzyl)uracil.

後処理

  1. customprepared
  2. customprepared
  3. additionit was added dropwise
  4. waitin 10 minutes
  5. stirringAfter 14 h under stirring
  6. customThe organic phase was separated by decantation
  7. extractionthe aqueous phase was extracted with dichloromethane (3×50 ml)
  8. washThe collected organic phases were washed with saturated sodium hydrogenocarbonate solution (25 ml), with water (25 ml) and with an aqueous saturated sodium chloride solution (25 ml)
  9. dry with materialThe organic phase was dried over sodium sulfate
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-acc159f6cf094af0b1ef62a16ff553a4
出典データセット
uspto-grants-2005_06
特許番号
US06911450B1

関連ノート

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