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Ethyl Acetate → 2-Butoxy-8-methoxy-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-6-amine

HRID 1010933
ノート
印刷プレビュー

反応式

HRID 1010933 の反応式
FC(F)(F)C(O)=O.[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].CS(O[CH2:30][CH:31]1[CH2:35][CH2:34][O:33][CH2:32]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O.O.[Cl-].[Na+].O>[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:30][CH:31]2[CH2:35][CH2:34][O:33][CH2:32]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 22273010(Tetrahydrofuran-3-yl)methyl methanesulfonateHCID 178450370HCID 178450370、化合物

生成物 1

HCID 576996032-Butoxy-8-methoxy-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-6-amine収率 101.5%

試薬・触媒・溶媒 3

HCID 679
Dimethyl Sulfoxide
溶媒
HCID 962Water溶媒
HCID 57417360Sodium chloride; water溶媒

反応条件

温度
60 °C

実験手順

A solution of 2-butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (4.5 g), tetrahydro-3-furanylmethyl methanesulfonate (2.77 g) and potassium carbonate (5.31 g) in dimethyl sulfoxide (45 ml) was stirred and heated at 60° C. for 1.5 hours, followed by heating at 90° C. for 2.5 hours. The reaction was allowed to cool and the mixture diluted with water and brine, and shaken with ethyl acetate. The insoluble solid present was filtered (209 mg of product) and the organic layer separated. The aqueous layer was further extracted four times with ethyl acetate. The combined organic layers were washed with water and then brine. The organic layer was dried by passing through a hydrophobic frit and concentrated in vacuo to yield a light brown solid (4.18 g). This was recrystallised from acetonitrile (25 ml) to afford the product (2.28 g). This was further purified by dissolving in dichloromethane and washing with 1M hydrochloric acid, brine and saturated sodium hydrogencarbonate. The organic layer was dried through a hydrophobic frit and concentrated in vacuo to yield the product as a cream coloured solid (2.03 g).

後処理

  1. temperatureby heating at 90° C. for 2.5 hours
  2. temperatureto cool
  3. filtrationThe insoluble solid present was filtered (209 mg of product)
  4. customthe organic layer separated
  5. extractionThe aqueous layer was further extracted four times with ethyl acetate
  6. washThe combined organic layers were washed with water
  7. customThe organic layer was dried
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-45682bb96d5340fdb55fa7c8f0cf37fb
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07977344B2

反応ノート

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