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

반응식

HRID 38546 반응식
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]

참가 물질

6

반응물 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

생성물 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-amine수율 58.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-fccfc73a97bd4aea90a59c399293f87b
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524722B2

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