Diethyl Ether → Tert-butyl 2-(2-(2-methylpyridin-4-yl)pyrimidin-5-yl)acetate

HRID 592200ノート

反応式

HRID 592200 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([CH3:14])[CH:9]=2)=[N:6][CH:7]=1.[Cl-].[C:16]([O:20][C:21](=[O:24])[CH2:22][Zn+])([CH3:19])([CH3:18])[CH3:17].CCOCC>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].CC(P(C(C)(C)C)[C-]1C=CC=C1)(C)C.C1C=CC([C-]2C(C3C=CC=CC=3)=C(C3C=CC=CC=3)C(C3C=CC=CC=3)=C2C2C=CC=CC=2)=CC=1.[Fe+2].C1COCC1>[CH3:14][C:10]1[CH:9]=[C:8]([C:5]2[N:4]=[CH:3][C:2]([CH2:22][C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:24])=[CH:7][N:6]=2)[CH:13]=[CH:12][N:11]=1

参加物

7

反応物 3

HCID 3283Diethyl EtherHCID 584476465-Bromo-2-(2-methylpyridin-4-yl)pyrimidineHCID 178451183HCID 178451183、化合物

生成物 1

HCID 58447797Tert-butyl 2-(2-(2-methylpyridin-4-yl)pyrimidin-5-yl)acetate

試薬・触媒・溶媒 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 129828017Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

To a sealed tube were added 5-bromo-2-(2-methylpyridin-4-yl)pyrimidine 183-3 (50 mg, 0.20 mmol), 0.5 M (2-tert-butoxy-2-oxoethyl) zinc(II) chloride in ether (0.60 mL, 0.30 mmol), Pd(dba)2 (6 mg, 0.01 mmol), Q-phos (14 mg, 0.02 mmol) and THF (1.5 mL). The reaction mixture was bubbled with nitrogen for 1 minute and stirred at 100° C. for 1 hour. After cooling to room temperature, all the solvents were evaporated and the residue was redissolved in ethyl acetate, washed with water and brine, dried over Na2SO4 and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography and eluted with 25% ethyl acetate in hexane to give tert-butyl 2-(2-(2-methylpyridin-4-yl)pyrimidin-5-yl)acetate 183-4. MS m/z 286.2 (M+1).

後処理

  1. customThe reaction mixture was bubbled with nitrogen for 1 minute
  2. temperatureAfter cooling to room temperature
  3. customall the solvents were evaporated
  4. dissolutionthe residue was redissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness by rotary evaporation
  8. customThe crude product was purified by silica gel flash chromatography
  9. washeluted with 25% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-aa50bf68056a4203b014a70259ec8e5f
出典データセット
uspto-grants-2016_01
特許番号
US09238646B2

反応ノート

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