Sodium Carbonate → 2,4-Dimethoxy-5-pyrazin-2-yl-pyrimidine

HRID 12743

反応式

HRID 12743 の反応式
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6](B(O)O)=[CH:5][N:4]=1.I[C:15]1[CH:20]=[N:19][CH:18]=[CH:17][N:16]=1.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]>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([C:15]2[CH:20]=[N:19][CH:18]=[CH:17][N:16]=2)=[CH:5][N:4]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 642841IodopyrazineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

生成物 1

HCID 589942062,4-Dimethoxy-5-pyrazin-2-yl-pyrimidine収率 45.4%

試薬・触媒・溶媒 2

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

実験手順

2,4-Dimethoxy-pyrimidine-5-boronic acid (1.33 g, 7.27 mmol) was dissolved in degassed n-PrOH (20 ml) and then 2-iodo-pyrazine (1.0 g, 4.85 mmol), Na2CO3 (1.02 g, 9.70 mmol), PPh3 (127 mg, 0.48 mmol) and Pd(OAc)2 (54 mg) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography eluting with DCM-MeOH—NH4OH (99-1-0.1) to give 481 mg of the title compound (45% yield).

後処理

  1. temperatureat reflux for 4 hours
  2. customThe solvent was evaporated under vacuum
  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
  7. washeluting with DCM-MeOH—NH4OH (99-1-0.1)

出典と根拠

ORDレコード
ord-d9b136ad99c54c0f9e509de38773057c
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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