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Formamide → Ethyl 4-oxo-3,4,5,7-tetrahydro-6H-pyrrolo[3',4':4,5]thieno[2,3-d]pyrimidine-6-carboxylate

HRID 38521
ノート
印刷プレビュー

反応式

HRID 38521 の反応式
[NH2:1][C:2]1[S:14][C:5]2[CH2:6][N:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][C:4]=2[C:3]=1[C:15]([O:17]CC)=O.C([O-])=O.[NH4+].[CH:24]([NH2:26])=O>O>[O:17]=[C:15]1[NH:26][CH:24]=[N:1][C:2]2[S:14][C:5]3[CH2:6][N:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][C:4]=3[C:3]1=2
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 713FormamideHCID 2723923Ammonium formateHCID 22464559Diethyl 2-amino-4,6-dihydro-5H-thieno[2,3-c]pyrrole-3,5-dicarboxylate

生成物 1

HCID 58116983Ethyl 4-oxo-3,4,5,7-tetrahydro-6H-pyrrolo[3',4':4,5]thieno[2,3-d]pyrimidine-6-carboxylate収率 52%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

Diethyl 2-amino-4,6-dihydro-5H-thieno[2,3-c]pyrrole-3,5-dicarboxylate from Example 19A (3.60 g, 12.7 mmol) was dissolved in formamide (72 mL), and ammonium formiate (2.11 g, 20.3 mmol) was added. The mixture was heated to 140° C. overnight, then diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was removed in vacuo. The precipitate in the aqueous layer was collected by suction filtration and combined with the organic extracts. The product was purified by column chromatography on silica gel (eluent: DCM/MeOH 100:3) and subsequently triturated with tert-butyl methyl ether to yield 1.74 g (52%) of the title compound.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was removed in vacuo
  4. filtrationThe precipitate in the aqueous layer was collected by suction filtration
  5. customThe product was purified by column chromatography on silica gel (eluent: DCM/MeOH 100:3)
  6. customsubsequently triturated with tert-butyl methyl ether

出典と根拠

ORDレコード
ord-8f196d1a7e684c90ac905bf95ac8b7f5
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08524722B2

反応ノート

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