Bromobenzene → 5-(3-fluoro-4-methoxyphenyl)-N-phenylpyrimidin-2-amine

HRID 1993353ノート

反応式

HRID 1993353 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[N:12][C:13]([NH2:16])=[N:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[N:14][C:13]([NH:16][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

参加物

6

反応物 3

HCID 7961BromobenzeneHCID 23665647Potassium tert-butoxideHCID 574453925-(3-Fluoro-4-methoxyphenyl)pyrimidin-2-amine

生成物 1

HCID 574453935-(3-fluoro-4-methoxyphenyl)-N-phenylpyrimidin-2-amine

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
200 °C

実験手順

A mixture of 5-(3-fluoro-4-methoxyphenyl)pyrimidin-2-amine (Step 1, 0.44 g, 2.0 mmol) and bromobenzene (0.60 g, 4.0 mmol) in N,N′-dimethylacetamide (1.0 mL) and toluene (1.0 mL) was placed in a microwave tube and was treated with Pd(OAc)2 (0.024 g, 0.1 mmol), 2-biscyclohexyl 1,1-biphenyl phosphine (Strem Chemical, 0.070 g, 0.20 mmol), and KOtBu (0.44 g, 4.0 mmol). The mixture was degassed with N2 (2×) and was subject to microwave heating at 200° C. for a total of 20 min. After the mixture was cooled to RT, it was filtered through a pad of Celite®. The solid was washed with EtOAc (3×10 mL), and the combined organic phase was washed with H2O, NH4Cl (sat.), dried with Na2SO4, and concentrated to an oil. Purification on silica using hexanes-EtOAc (3:1) resulted the desired compound as a yellow solid. MS (ESI pos. ion) m/z: 296. Calc'd for C17H14FN3O: 295.11.

後処理

  1. customwas placed in a microwave tube
  2. customThe mixture was degassed with N2 (2×)
  3. temperatureAfter the mixture was cooled to RT
  4. filtrationit was filtered through a pad of Celite®
  5. washThe solid was washed with EtOAc (3×10 mL)
  6. washthe combined organic phase was washed with H2O, NH4Cl (sat.)
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated to an oil
  9. customPurification on silica

出典と根拠

ORDレコード
ord-174c86706a9b45e39020fbeac83a63eb
出典データセット
uspto-grants-2010_01
特許番号
US07652009B2

反応ノート

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