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Tetramethyltin → 4-(2-Methoxyethoxy)-2-(6-methylpyridin-3-yl)-6-(pyrazolo[1,5-a]pyridin-3-ylcarbonyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 452584
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HRID 452584 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([O:29][CH2:30][CH2:31][O:32][CH3:33])[C:11]3[CH2:17][N:16]([C:18]([C:20]4[CH:21]=[N:22][N:23]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=45)=[O:19])[CH2:15][CH2:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[CH3:34][Sn](C)(C)C>CN(C=O)C.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>[CH3:33][O:32][CH2:31][CH2:30][O:29][C:10]1[C:11]2[CH2:17][N:16]([C:18]([C:20]3[CH:21]=[N:22][N:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=34)=[O:19])[CH2:15][CH2:14][C:12]=2[N:13]=[C:8]([C:5]2[CH:6]=[N:7][C:2]([CH3:34])=[CH:3][CH:4]=2)[N:9]=1
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참가 물질

5

반응물 2

HCID 11661TetramethyltinHCID 49821989[2-(6-Chloropyridin-3-yl)-4-(2-methoxyethoxy)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5h)-yl](pyrazolo[1,5-a]pyridin-3-yl)methanone

생성물 1

HCID 498220734-(2-Methoxyethoxy)-2-(6-methylpyridin-3-yl)-6-(pyrazolo[1,5-a]pyridin-3-ylcarbonyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine수율 49%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

To a solution of 30 mg (0.065 mmol) O-2 in 1 mL DMF in a microwave vial was added approximately 20 uL (˜0.15 mmol) tetramethyltin and 8 mg (˜10 mol %) tetrakistriphenylphosphinepalladium(0). The reaction was heated by microwave irradiation for 20 minutes at 150° C. After cooling, the reaction was purified by reverse phase HPLC (CH3CN/H2O with TFA as modifier), and the fractions containing the product were partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to provide R-1 as a white solid (14 mg, 49% yield). HRMS m/z (M+H) 445.1977 found, 445.1983 required.

후처리

  1. temperatureAfter cooling
  2. customthe reaction was purified by reverse phase HPLC (CH3CN/H2O with TFA as modifier)
  3. additionthe fractions containing the product
  4. customwere partitioned between EtOAc and saturated aqueous NaHCO3
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f67e3aa8cdcc486596c9da51813412aa
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492392B2

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