Thionyl Chloride → 7-[(2E)-4-Chlorobut-2-enoyl]-N-(3,4-dichlorophenyl)-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

HRID 38546

反応式

HRID 38546 の反応式
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([OH:7])=O.S(Cl)([Cl:10])=O.[Cl:12][C:13]1[CH:14]=[C:15]([NH:20][C:21]2[C:22]3[C:29]4[CH2:30][CH2:31][NH:32][CH2:33][C:28]=4[S:27][C:23]=3[N:24]=[CH:25][N:26]=2)[CH:16]=[CH:17][C:18]=1[Cl:19].CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:10][CH2:2]/[CH:3]=[CH:4]/[C:5]([N:32]1[CH2:31][CH2:30][C:29]2[C:22]3[C:21]([NH:20][C:15]4[CH:16]=[CH:17][C:18]([Cl:19])=[C:13]([Cl:12])[CH:14]=4)=[N:26][CH:25]=[N:24][C:23]=3[S:27][C:28]=2[CH2:33]1)=[O:7]

参加物

6

反応物 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 64364114-Bromocrotonic acidHCID 58116912(3,4-Dichloro-phenyl)-(5,6,7,8-tetrahydro-9-thia-1,3,7-triaza-fluoren-4-yl)-amine

生成物 1

HCID 581168067-[(2E)-4-Chlorobut-2-enoyl]-N-(3,4-dichlorophenyl)-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine収率 58.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(2E)-4-Bromobut-2-enoic acid (1.33 g, 6.83 mmol) was dissolved in petroleum ether (25 mL). Thionylchloride (2.65 mL, 36.6 mmol) was added, and the mixture was heated to reflux for 4 h. The mixture was then concentrated in vacuo. Toluene was added and again removed in vacuo. The residue was dissolved in dichloromethane (14 mL). This solution was added to a solution of N-(3,4-dichlorophenyl)-5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-amine from Example 15A (2.00 g, 5.69 mmol) and DIPEA (1.25 g, 9.68 mmol) in DMF (20 mL) at −10° C. The mixture was warmed to rt and stirred overnight. The precipitate was collected by suction filtration and washed with water to yield 1.52 g of a solid, which was used in the next step without further purification or separation.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. concentrationThe mixture was then concentrated in vacuo
  4. additionToluene was added
  5. customagain removed in vacuo
  6. dissolutionThe residue was dissolved in dichloromethane (14 mL)
  7. filtrationThe precipitate was collected by suction filtration
  8. washwashed with water

出典と根拠

ORDレコード
ord-fccfc73a97bd4aea90a59c399293f87b
出典データセット
uspto-grants-2013_09
特許番号
US08524722B2

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