Potassium Phosphate, Tribasic → 5-(3-fluoro-4-methoxyphenyl)-3-methyl-2-methylthio-3H-pyrimidin-4-one

HRID 1993346

反応式

HRID 1993346 の反応式
Br[C:2]1[C:3](=[O:11])[N:4]([CH3:10])[C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:12][C:13]1[CH:14]=[C:15]([C:2]2[C:3](=[O:11])[N:4]([CH3:10])[C:5]([S:8][CH3:9])=[N:6][CH:7]=2)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 32646665-Bromo-3-methyl-2-(methylthio)pyrimidin-4(3H)-oneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

生成物 1

HCID 588288915-(3-fluoro-4-methoxyphenyl)-3-methyl-2-methylthio-3H-pyrimidin-4-one

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

5-Bromo-3-methyl-2-methylthio-4(3H)-pyrimidinone (Step 3, 14.77 g, 62.8 mmol), 3-fluoro-4-methoxyphenylboronic acid (20.11 g, 118.3 mmol), Pd2(dba)3 (1.869 g, 2.04 mmol), S-phos ligand (Strem Chemical, 3.45 g, 8.40 mmol) and K3PO4 (42.27 g, 199.1 mmol) were suspended in toluene (200 mL). Ar was bubbled through the solution for 5 min, and the reaction was placed in an oil bath (100° C.) and stirred for 6.25 h, at which time LCMS analysis indicated a complete reaction. The reaction was cooled to RT and allowed to stand overnight. It was diluted with CH2Cl2 (200 mL) and filtered through a 1-inch plug of silica gel which was washed exhaustively with MeOH, EtOAc, and CH2Cl2. (Some solid material stuck in the flask had to be taken up in water and extracted with EtOAc separately). The filtrate (and EtOAc extracts) were all combined and concentrated, resulting in an orange solid. This was treated with hexanes and filtered, and the resultant light yellow solid was washed repeatedly with hexanes and then put on the high vacuum overnight. The title compound was obtained as a light yellow solid. MS (ESI pos. ion) m/z: 281. Calc'd for C13H13FN2O2S: 280.07.

後処理

  1. customAr was bubbled through the solution for 5 min
  2. customthe reaction was placed in an oil bath
  3. customa complete reaction
  4. temperatureThe reaction was cooled to RT
  5. waitto stand overnight
  6. filtrationfiltered through a 1-inch plug of silica gel which
  7. washwas washed exhaustively with MeOH, EtOAc, and CH2Cl2
  8. extractionextracted with EtOAc separately)
  9. concentrationconcentrated
  10. customresulting in an orange solid
  11. filtrationfiltered
  12. washthe resultant light yellow solid was washed repeatedly with hexanes
  13. customput on the high vacuum overnight

出典と根拠

ORDレコード
ord-23150f509d7e4c9dbff5600ad6ec2017
出典データセット
uspto-grants-2010_01
特許番号
US07652009B2

関連ノート

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