Sodium Carbonate → 2,4-Dimethoxy-5-o-tolyl-pyrimidine

HRID 12683

反応式

HRID 12683 の反応式
I[C:2]1[C:3]([O:10][CH3:11])=[N:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.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]>[CH3:9][O:8][C:5]1[N:4]=[C:3]([O:10][CH3:11])[C:2]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH3:12])=[CH:7][N:6]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2634165-Iodo-2,4-dimethoxypyrimidineHCID 27332672-Methylphenyl boronic acid

生成物 1

HCID 398263862,4-Dimethoxy-5-o-tolyl-pyrimidine収率 46.3%

試薬・触媒・溶媒 2

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

実験手順

5-Iodo-2,4-dimethoxy-pyrimidine (1 g, 3.75 mmol) was dissolved in degassed n-PrOH (25 mL) and then 2-methylphenyl boronic acid (766 mg, 3.8 mmol), Na2CO3 (865 mg, 8.16 mmol), PPh3 (215 mg, 0.8 mmol) and Pd(OAc)2 (50 mg, 5.67 mmol) were added. The suspension was stirred at reflux for 3 hours. The solvent was evaporated and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-9) to give 400 mg of the title compound (46% yield).

後処理

  1. temperatureat reflux for 3 hours
  2. customThe solvent was evaporated
  3. customthe crude was partitioned between water and DCM
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-9)

出典と根拠

ORDレコード
ord-9a8cf9b2892e4ae19622ca043b60c59e
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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