Sodium Carbonate → 3-(2,4-Dimethoxy-pyrimidin-5-yl)-pyridine-2-carbonitrile

HRID 12726

反応式

HRID 12726 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.[C:14]([C:16]1[C:21](Br)=[CH:20][CH:19]=[CH:18][N:17]=1)#[N:15].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:21]2[C:16]([C:14]#[N:15])=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:5][N:4]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 8176943-Bromopyridine-2-carbonitrileHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

生成物 1

HCID 589942323-(2,4-Dimethoxy-pyrimidin-5-yl)-pyridine-2-carbonitrile収率 79.5%

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 g, 5.46 mmol) was dissolved in degassed n-PrOH (30 ml) and then 2-cyano-3-bromopyridine (950 mg, 5.19 mmol), Na2CO3 (1.65 g, 15.56 mmol), PPh3 (393 mg, 1.5 mmol) and Pd(OAc)2 (114 mg, 0.51 mmol) were added. The suspension was stirred at reflux for 3 hours. After cooling, the solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase washed with brine, dried (Na2SO4) and evaporated. The residue was triturated with iPrOH to give 1 g of the title compound as a white powder (76% yield).

後処理

  1. temperatureat reflux for 3 hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated under vacuum
  4. customthe crude was partitioned between water and ethyl acetate
  5. washThe organic phase washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was triturated with iPrOH

出典と根拠

ORDレコード
ord-479b3529179947c7ae9108e5afb47566
出典データセット
uspto-grants-2010_06
特許番号
US07727988B2

関連ノート

読み込み中…