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

HRID 928619

反応式

HRID 928619 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-641d821350604458831a0a0cddebb5c9
出典データセット
uspto-grants-2016_03
特許番号
US09290511B2

関連ノート

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