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Water → cis-1-{[6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}pyrrolidine-3,4-diol

HRID 2171811
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HRID 2171811 반응식
CS(O[CH2:6][C:7]1[C:8]2[CH:16]=[C:15]([CH:17]3[CH2:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19][CH2:18]3)[S:14][C:9]=2[N:10]=[C:11]([CH3:13])[N:12]=1)(=O)=O.Cl.[NH:26]1[CH2:30][C@H:29]([OH:31])[C@H:28]([OH:32])[CH2:27]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:23][C:20]1([CH3:24])[CH2:21][CH2:22][CH:17]([C:15]2[S:14][C:9]3[N:10]=[C:11]([CH3:13])[N:12]=[C:7]([CH2:6][N:26]4[CH2:30][C@H:29]([OH:31])[C@H:28]([OH:32])[CH2:27]4)[C:8]=3[CH:16]=2)[CH2:18][CH2:19]1
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참가 물질

6

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HCID 962WaterHCID 11430Potassium CarbonateHCID 21970171(3S,4R)-pyrrolidine-3,4-diol hydrochlorideHCID 118023751[6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate

생성물 1

HCID 118023762cis-1-{[6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}pyrrolidine-3,4-diol수율 8.8%

시약·촉매·용매

1
HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

A suspension of [6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate (100 mg), cis-pyrrolidine-3,4-diol hydrochloride (57 mg), and K2CO3 (75 mg) in DMF (3 mL) was stirred at 50° C. for 12 hours. The reaction mixture was cooled to room temperature, and water was added thereto, followed by extraction with EtOAc. The organic layer was dried over MgSO4 and then concentrated under reduced pressure. The residue was purified by silica gel column (chloroform/MeOH). The obtained purified product was suspended in IPE, and the precipitate was collected by filtration to obtain cis-1-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}pyrrolidine-3,4-diol (9 mg).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column (chloroform/MeOH)
  6. customThe obtained purified product
  7. filtrationthe precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-1421a5473a564f64af0dde8e02e88006
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09051339B2

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