Sodium Carbonate → 1-Benzhydryl-5-phenyl-pyrimidine-2,4-dione

HRID 1486533ノート

反応式

HRID 1486533 の反応式
[CH:1]([N:14]1[CH:19]=[C:18](I)[C:17](=[O:21])[NH:16][C:15]1=[O:22])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1(C)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>CCOC(C)=O.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:1]([N:14]1[CH:19]=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17](=[O:21])[NH:16][C:15]1=[O:22])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 21863594Toluene ethanolHCID 716549651-Benzhydryl-5-iodo-pyrimidine-2,4-dione

生成物 1

HCID 900178241-Benzhydryl-5-phenyl-pyrimidine-2,4-dione収率 62%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

1-Benzhydryl-5-iodo-pyrimidine-2,4-dione (0.06 g, 0.15 mmol) was suspended in a 1:1 toluene/ethanol mixture (1,6 Phenylboronic acid (0.03 g, 0.22 mmol) was added followed by 2M aqueous solution of sodium carbonate (0.082 mL, 0.16 mmol). The resulting suspension was degassed under nitrogen atmosphere for 10 min, then tetrakis(triphenylphosphine) palladium(0) (0.017 g, 0.015 mmol) was added. The reaction was heated under microwave irradiation at 100° C. for 30 min. The reaction mixture was diluted with EtOAc and water was added. The two phases were separated and the aqueous layer was extracted with EtOAc (3×15 mL). The combined organic phases were dried over Na2SO4 and the solvent was removed under reduced pressure. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 60:40) to afford the title compound (0.03 g, 62%) as pale yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.13 (s, 1H), 7.20-7.24 (m, 5H), 7.25 (s, 1H), 7.32-7.35 (m, 5H), 7.37-7.44 (m, 5H), 8.19 (br s, 1H). MS (ESI) to/z: 355 [M-H]+.

後処理

  1. additionwas added
  2. customThe resulting suspension was degassed under nitrogen atmosphere for 10 min
  3. additionwas added
  4. customThe two phases were separated
  5. extractionthe aqueous layer was extracted with EtOAc (3×15 mL)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. customthe solvent was removed under reduced pressure
  8. customThe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-20a472e1d2654df69a3beb3f6f2a7269
出典データセット
uspto-grants-2016_08
特許番号
US09428465B2

反応ノート

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