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Methyl thieno[2,3-d]pyrimidine-6-carboxylate → N-Methoxy-N-methylthieno[2,3-d]pyrimidine-6-carboxamide

HRID 32517
ノート
印刷プレビュー

反応式

HRID 32517 の反応式
C([Mg]Cl)(C)C.[N:6]1[C:11]2[S:12][C:13]([C:15]([O:17]C)=O)=[CH:14][C:10]=2[CH:9]=[N:8][CH:7]=1.[CH3:19][O:20][N-:21][CH3:22]>C1COCC1>[CH3:19][O:20][N:21]([CH3:22])[C:15]([C:13]1[S:12][C:11]2[N:6]=[CH:7][N:8]=[CH:9][C:10]=2[CH:14]=1)=[O:17]
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

5

反応物 3

HCID 17965832Methyl thieno[2,3-d]pyrimidine-6-carboxylate2 回HCID 53630747Methoxy-methyl amideHCID 178418918HCID 178418918、化合物

生成物 1

HCID 85929707N-Methoxy-N-methylthieno[2,3-d]pyrimidine-6-carboxamide収率 67.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

iPrMgCl (2M in THF, 1.1 mL) was added dropwise to a solution of methyl thieno[2,3-d]pyrimidine-6-carboxylate (intermediate 11) (138 mg) and N-methoxy-N-methylamide (104 mg) in THF at −20° C. maintaining the internal temperature below −5° C. The reaction was allowed to stir at −10° C. for 30 minutes and then quenched with NH4Cl (sat. aq). The solution was diluted with EtOAc and the organic layer was separated. The aqueous layer was extracted with EtOAc (2×15 mL) and then the combined organics dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with hexane:EtOAc (1:1 to 1:4) afforded the title compound as a pale yellow solid (107 mg, 67%);

後処理

  1. temperaturemaintaining the internal temperature below −5° C
  2. customquenched with NH4Cl (sat. aq)
  3. additionThe solution was diluted with EtOAc
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with EtOAc (2×15 mL)
  6. dry with materialthe combined organics dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica eluting with hexane:EtOAc (1:1 to 1:4)

出典と根拠

ORDレコード
ord-8a8883e797c94e98bb80a4a28619efad
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07427616B2

反応ノート

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