Sodium Carbonate → 2,4-Dimethoxy-5-(6-methyl-pyridin-3-yl)-pyrimidine

HRID 12687

反応式

HRID 12687 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.Br[C:15]1[CH:16]=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=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:16]=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=2)=[CH:5][N:4]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 12010205-Bromo-2-methylpyridineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

生成物 1

HCID 589941672,4-Dimethoxy-5-(6-methyl-pyridin-3-yl)-pyrimidine収率 62%

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 (commercially available from Aldrich, 830 mg, 4.5 mmol) was dissolved in degassed n-PrOH (10 mL) and then 3-bromo-6-methylpyridine (600 mg, 3.5 mmol), Na2CO3 (956 mg, 9 mmol), PPh3 (90 mg, 0.35 mmol) and Pd(OAc)2 (78 mg, 0.35 mmol) were added. The suspension was stirred at reflux for 1.5 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by SCX cartridge washing with MeOH and then collecting the product with MeOH—NH4OH (95-5) to give 500 mg of the title compound (62% yield).

後処理

  1. temperatureat reflux for 1.5 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe crude was partitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was purified by SCX cartridge
  7. washwashing with MeOH
  8. customcollecting the product with MeOH—NH4OH (95-5)

出典と根拠

ORDレコード
ord-467f17a6508d4a118f67db9676324ab1
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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