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Potassium Carbonate → 5-(2-Fluoro-3-pyridinyl)-2,4-bis(methyloxy)pyrimidine

HRID 12712
ノート
印刷プレビュー

反応式

HRID 12712 の反応式
Br[C:2]1[C:3]([O:10][CH3:11])=[N:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[F:12][C:13]1[C:18](B(O)O)=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+].B(O)O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O.O.O1CCOCC1>[F:12][C:13]1[C:18]([C:2]2[C:3]([O:10][CH3:11])=[N:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=2)=[CH:17][CH:16]=[CH:15][N:14]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 11430Potassium CarbonateHCID 61668Boronic AcidHCID 2557195-Bromo-2,4-dimethoxypyrimidineHCID 27832702-Fluoropyridine-3-boronic acid

生成物 1

HCID 589941555-(2-Fluoro-3-pyridinyl)-2,4-bis(methyloxy)pyrimidine収率 93.1%

試薬・触媒・溶媒 4

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a mixture of 5-bromo-2,4-bis(methyloxy)pyrimidine (Prep86, 3 g, 13.70 mmol), 2-fluoropyridine-3-boronic acid (1.930 g, 13.70 mmol) and Pd(PPh3)4 (0.791 g, 0.685 mmol), dry 1,4-Dioxane (45 ml) was added followed by potassium carbonate 1M solution (27.4 ml, 27.4 mmol). The mixture was degassed with Argon and then heated at 100° C. for 1 h (internal T˜90° C.). Then the mixture was cooled down to ambient, further 1 eq of boronic acid (1.930 g, 13.70 mmol) followed by 5 mol % of PdTetrakis (0.791 g, 0.685 mmol) were added and the mixture heated at 100° C. for two 2 h. The reaction mixture was cooled down to room temperature, taken up with water and AcOEt. The aqueous layer was back extracted with AcOEt. The combined organics were dried over Na2SO4 and evaporated to dryness. The crude material was purified by SiO2 flash chromatography eluting with Cy/EA 8/2 to get the title compound as white solid (3 g).

後処理

  1. additionwas added
  2. customThe mixture was degassed with Argon
  3. temperatureThen the mixture was cooled down
  4. additionwere added
  5. temperaturethe mixture heated at 100° C. for two 2 h
  6. temperatureThe reaction mixture was cooled down to room temperature
  7. extractionThe aqueous layer was back extracted with AcOEt
  8. dry with materialThe combined organics were dried over Na2SO4
  9. customevaporated to dryness
  10. customThe crude material was purified by SiO2 flash chromatography
  11. washeluting with Cy/EA 8/2

出典と根拠

ORDレコード
ord-c4c1cbbe3d4c4342ab9166f0952850e1
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07727988B2

反応ノート

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