1-Naphthalenecarbonyl chloride → 3-Methyl-1-(2-methylpropyl)-6-(1-naphthalenylcarbonyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 1611041

反応式

HRID 1611041 の反応式
[C:1]1([C:11](Cl)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:18][N:19]1[C:24](=[O:25])[C:23]2[CH:26]=[CH:27][S:28][C:22]=2[N:21]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:20]1=[O:33]>ClCCCl>[CH3:18][N:19]1[C:24](=[O:25])[C:23]2[CH:26]=[C:27]([C:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)=[O:12])[S:28][C:22]=2[N:21]([CH2:29][CH:30]([CH3:31])[CH3:32])[C:20]1=[O:33]

参加物

5

反応物 3

HCID 701461-Naphthalenecarbonyl chlorideHCID 52825273-Methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 222579723-Methyl-1-(2-methylpropyl)-6-(1-naphthalenylcarbonyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

実験手順

1-Naphthoyl chloride (1.25 ml) was added under nitrogen to a stirred slurry of aluminum chloride (1.1 g) in 1,2-dichloroethane (10 ml). A solution of 3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidin-2,4(1H,3H)-dione (2.0 g) in 1,2-dichloroethane (10 ml) was added dropwise and the resultant mixture was heated under reflux for 24 h and then allowed to cool to ambient temperature. The reaction mixture was quenched by the careful addition of water (2 ml) and was then concentrated in vacuo. The residue was dissolved in ethyl acetate and washed thrice with dilute hydrochloric acid, twice with saturated sodium hydrogen carbonate solution, and once with brine, then dried over magnesium sulfate and concentrated in vacuo. Purification by chromatography on silica gel eluting with toluene:ethyl acetate (9:1) gave the title compound (0.78 g).

後処理

  1. temperatureunder reflux for 24 h
  2. customThe reaction mixture was quenched by the careful addition of water (2 ml)
  3. concentrationwas then concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed thrice with dilute hydrochloric acid
  6. dry with materialtwice with saturated sodium hydrogen carbonate solution, and once with brine, then dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography on silica gel eluting with toluene:ethyl acetate (9:1)

出典と根拠

ORDレコード
ord-30f5ac9cf5de4b409ada5e7aced7d035
出典データセット
uspto-grants-2006_01
特許番号
US06984644B2

関連ノート

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