Dimethylformamide → HCID 86679606、化合物

HRID 577661ノート

反応式

HRID 577661 の反応式
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([F:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[N:7]=1.[N+:21]([C:24]1[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22].CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.O>[Cl:1][C:2]1[N:3]=[C:4]([O:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=2)[C:5]2[C:10]([F:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[N:7]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 86679607HCID 86679607、化合物

生成物 1

HCID 86679606HCID 86679606、化合物収率 99%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a vial containing 2,4-dichloro-5-fluoro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (389.5 mg, 1.2 mmol) was added m-nitrophenol (161 mg, 1.2 mmol), DMF (5 mL) and K2CO3 (320 mg, 2.3 mmol). The reaction mixture was heated at 60° C. for 1 hr. The reaction was diluted with EtOAc (120 mL) and water (30 mL). The organic layer was separated, washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and evaporated to give an oil. The oil was purified via flash chromatography eluting with 100% heptanes. The solvent was removed to afford the title compound (505 mg, 99% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.34 (t, J=2.27 Hz, 1H) 8.22-8.28 (m, 1H) 7.90-7.96 (m, 1H) 7.86 (d, J=8.31 Hz, 1H) 7.78-7.84 (m, 1H) 5.59 (s, 2H) 3.54-3.66 (m, 2H) 0.84-0.99 (m, 2H) 0.00 (s, 9H). m/z (APCI+) for C18H20ClFN4O4Si 439.1 (M+H)+.

後処理

  1. customThe organic layer was separated
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customto give an oil
  6. customThe oil was purified via flash chromatography
  7. washeluting with 100% heptanes
  8. customThe solvent was removed

出典と根拠

ORDレコード
ord-6ee0c219ec4e46ed8e450057aff85d56
出典データセット
uspto-grants-2015_05
特許番号
US09040547B2

反応ノート

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