Ethanol → (5-Bromothieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamine

HRID 910202ノート

反応式

HRID 910202 の反応式
[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1.C(O)C.C(N(CC)CC)C.[NH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1>O>[Br:1][C:2]1[C:10]2[C:9]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1

参加物

6

反応物 4

HCID 702EthanolHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 454802995-Bromo-4-chlorothieno[2,3-d]pyrimidine

生成物 1

HCID 67381984(5-Bromothieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamine収率 63.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A stirred mixture of 5-bromo-4-chlorothieno[2,3-d]pyrimidine (3.8 g, 15.2 mmol), ethanol (250 ml), triethylamine (2.32 ml, 16.7 mmol) and 2-aminomethylpyridine (1.72 ml, 16.7 mmol) was heated under reflux for 2.5 hours. The solution was then cooled to ambient temperature, poured into water (300 ml) and extracted with dichloromethane (3×150 ml). The combined organic extracts were dried (MgSO4) and the solvent removed in vacuo to give the crude product. Purification by flash chromatography (silica) eluting with ethyl acetate and 40°-60° petroleum ether (1:1) gave (5-bromothieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamine as a yellow solid (3.12 g), m.pt. 127°-129° C.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. extractionextracted with dichloromethane (3×150 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give the crude product
  7. customPurification by flash chromatography (silica)
  8. washeluting with ethyl acetate and 40°-60° petroleum ether (1:1)

出典と根拠

ORDレコード
ord-71d2c6e6e7b84271b2054899a74236be
出典データセット
uspto-grants-2011_09
特許番号
US08022076B2

反応ノート

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