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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
ノート
印刷プレビュー

反応式

HRID 452584 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 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]pyrimidine収率 49%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f67e3aa8cdcc486596c9da51813412aa
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08492392B2

反応ノート

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