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Sodium Carbonate → 1-(4-Benzo[1,3]dioxol-5-yl-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol

HRID 1161672
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HRID 1161672 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]2)[N:3]=1.[C:21](=[O:24])([O-])[O-:22].[Na+].[Na+]>CN(C)C=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:22]1[C:9]2[CH:10]=[CH:11][C:12]([C:2]3[CH:7]=[C:6]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[N:5]=[C:4]([N:14]4[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]4)[N:3]=3)=[CH:13][C:8]=2[O:24][CH2:21]1
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참가 물질

6

반응물 2

HCID 10340Sodium CarbonateHCID 586261271-(4-Chloro-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol

생성물 1

HCID 114945441-(4-Benzo[1,3]dioxol-5-yl-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매
HCID 6228
Dimethylformamide
용매

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온도
25 °C

실험 절차

A mixture of compound benzo[1,3]dioxo-5-yl boronic acid (0.14 g, 83 mmol), and compound 1-(4-chloro-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol (90.2 g, 69 mmol), (PPh3)4Pd (31 mg, 0.03 mmol) and sodium carbonate (0.73 g, 69 mmol) in dimethylformamide (5 mL) was stirred for 1 hour at 25° C. and then for 12 hours at 80° C. under nitrogen atmosphere. The mixture was cooled to temperature in the range of 20-40° C., diluted with water (10 mL) and extracted with ethyl acetate (3×10 mL). The organic layers were collected, combined, washed with water (10 mL), dried over anhydrous sodium sulphate, and concentrated under vacuum. The residue thus obtained was purified by column chromatography using ethyl acetate-petroleum ether to give the desired compound.

후처리

  1. waitfor 12 hours at 80° C. under nitrogen atmosphere
  2. temperatureThe mixture was cooled to temperature in the range of 20-40° C.
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. customThe organic layers were collected
  5. washwashed with water (10 mL)
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under vacuum
  8. customThe residue thus obtained
  9. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-6203cb15243e4698badfaf7fb1e7692b
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07820654B2

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