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Sodium Carbonate → 4-(2-Fluoro-phenyl)-2-methylsulfanyl-pyrimidine

HRID 1514431
ノート
印刷プレビュー

反応式

HRID 1514431 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 971134-Chloro-2-methylthiopyrimidineHCID 27343542-Fluorophenylboronic acid

生成物 1

HCID 592427874-(2-Fluoro-phenyl)-2-methylsulfanyl-pyrimidine収率 90%

試薬・触媒・溶媒 2

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

実験手順

To a solution of 4-chloro-2-methylsulfanyl-pyrimidine (1.00 g, 6.22 mmol), 2-fluoro-phenyl-boronic acid (1.04 g, 6.84 mmol), Na2CO3 (790 mg, 7.45 mmol), triphenylphosphine (163 mg, 0.62 mmol) in nPrOH (50 ml), Pd(OAc)2 (42 mg, 0.187 mmol) was added and the mixture was refluxed for 3 hours. The solvent was evaporated under vacuum, and the crude was dissolved in ethyl acetate and washed with water. The organic phase was dried (Na2SO4) and evaporated; the crude was purified by flash chromatography with petroleum ether-ethyl acetate (97-3 to 95-5) to give the title compound (1.23 g, 90% yield).

後処理

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThe solvent was evaporated under vacuum
  3. dissolutionthe crude was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated
  7. customthe crude was purified by flash chromatography with petroleum ether-ethyl acetate (97-3 to 95-5)

出典と根拠

ORDレコード
ord-d75b0e9e055c4634b925646c60f3d7e8
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08222266B2

反応ノート

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