Sodium Carbonate → 2,4-Ditert-butoxy-5-(3-methyl-2-thienyl)pyrimidine

HRID 12660

反応式

HRID 12660 の反応式
[C:1]([O:5][C:6]1[N:11]=[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9](B(O)O)=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:21]1[S:22][CH:23]=[CH:24][C:25]=1[CH3:26].C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([O:5][C:6]1[N:11]=[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]([C:21]2[S:22][CH:23]=[CH:24][C:25]=2[CH3:26])=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 843142-Bromo-3-methylthiopheneHCID 2735950(2,4-Di-tert-butoxypyrimidin-5-yl)boronic acid

生成物 1

HCID 44586132,4-Ditert-butoxy-5-(3-methyl-2-thienyl)pyrimidine収率 32%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 10311-Propanol溶媒

実験手順

2,4-Di-tert-butoxy-pyrimidine-5-boronic acid (500 mg, 1.75 mmol) was dissolved in n-PrOH (5 mL) and then 2-bromo-3-methylthiophene (236 μl, 2.1 mmol), Na2CO3 (556 mg, 5.25 mmol), PPh3 (133 mg, 0.52 mmol) and Pd(OAc)2 (40 mg, 0.17 mmol) were added. The suspension was stirred at reflux for 2.5 hours. The solvent was evaporated and the crude was dissolved in water and extracted with Et2O. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-99) to give 170 mg of the title compound as a white solid (32% yield).

後処理

  1. temperatureat reflux for 2.5 hours
  2. customThe solvent was evaporated
  3. dissolutionthe crude was dissolved in water
  4. extractionextracted with Et2O
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated
  7. customThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-99)

出典と根拠

ORDレコード
ord-6a27ead10db740a4ac7fefbba65f9c12
出典データセット
uspto-grants-2010_06
特許番号
US07727988B2

関連ノート

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