Tetrahydrofuran → 8-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-8-azabicyclo[3.2.1]octan-3-ol

HRID 928619노트

반응식

HRID 928619 반응식
O1CCCC1.C(N(CC)CC)C.[Cl:13][C:14]1[N:15]=[C:16](Cl)[C:17]2[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:21][S:20][C:18]=2[N:19]=1.[CH:30]12[NH:37][CH:34]([CH2:35][CH2:36]1)[CH2:33][CH:32]([OH:38])[CH2:31]2>O.C(OCC)(=O)C>[Cl:13][C:14]1[N:15]=[C:16]([N:37]2[CH:30]3[CH2:36][CH2:35][CH:34]2[CH2:33][CH:32]([OH:38])[CH2:31]3)[C:17]2[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:21][S:20][C:18]=2[N:19]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 681478-Azabicyclo[3.2.1]octan-3-olHCID 127242282,4-Dichloro-5-phenylthieno(2,3-d)pyrimidine

생성물 1

HCID 895795888-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-8-azabicyclo[3.2.1]octan-3-ol수율 95.9%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

Tetrahydrofuran (2 mL) and triethylamine (0.10 mL, 0.71 mmol) were added to 2,4-dichloro-5-phenyl-thieno[2,3-d]pyrimidine (100 mg, 0.356 mmol) and 8-azabicyclo[3.2.1]octan-3-ol (68 mg, 0.53 mmol). The mixture was stirred overnight at room temperature. Ethyl acetate (2 mL) and water (2 mL) were added and the layers were separated. The aqueous was extracted with ethyl acetate (2×2 mL). The combined organic layers were dried (magnesium sulfate), filtered and evaporated to give a brown solid (127 mg). This was purified by silica chromatography (10 g cartridge; eluent petroleum ether 40-60/ethyl acetate 0 to 30%; all output collected). One set of fractions was identified and the relevant fractions were combined and evaporated to give a brown solid (83 mg). This was purified again by LCUV (acidic method 1) to give the target compound as a white solid (44 mg). m/z [M+H]+372.0/373.9. Retention time 4.74 min (LCMS method+ve 6 min).

후처리

  1. customthe layers were separated
  2. extractionThe aqueous was extracted with ethyl acetate (2×2 mL)
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-641d821350604458831a0a0cddebb5c9
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290511B2

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