Sodium Carbonate → Methyl 2-(4-((2-cyclopentyl-6-ethylpyrimidin-4-yl)methyl)phenyl)acetate

HRID 1508932ノート

反応式

HRID 1508932 の反応式
Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:3]=1.CC1(C)C(C)(C)OB([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:26][CH:25]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:10]1([C:4]2[N:3]=[C:2]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:28][CH:29]=3)[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=2)[CH2:11][CH2:12][CH2:13][CH2:14]1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 609214014-Chloro-2-cyclopentyl-6-ethylpyrimidineHCID 674944814-(2-Methoxy-2-oxoethyl)benzylboronic Acid Pinacol Ester

生成物 1

HCID 90109465Methyl 2-(4-((2-cyclopentyl-6-ethylpyrimidin-4-yl)methyl)phenyl)acetate収率 14%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A mixture of 4-chloro-2-cyclopentyl-6-ethylpyrimidine (0.275 g, 0.95 mmol), methyl 2-(4-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)phenyl)acetate (0.200 g, 0.95 mmol), Pd(dppf)Cl2 (0.078 g, 0.095 mmol), and powdered Na2CO3 (0.302 g, 2.85 mmol) in dioxane (5 mL) and water (3 mL) was stirred under an argon atmosphere at 90° C. for 48 h. After this time, the mixture was cooled and filtered through celite washing with ethyl acetate. The filtrate was washed with brine (3×15 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica, hexane/ethyl acetate) to afford the title compound (0.027 g, 14%) as a brown oil. MW=338.44. 1H NMR (DMSO-d6, 500 MHz) δ 7.28-7.22 (m, 2H), 7.21-7.17 (m, 2H), 7.01 (s, 1H), 3.96 (s, 2H), 3.63 (s, 2H), 3.59 (s, 3H), 3.21 (quin, J=8.1 Hz, 1H), 2.63 (q, J=7.6 Hz, 2H), 2.01-1.90 (m, 2H), 1.88-1.79 (m, 2H), 1.78-1.70 (m, 2H), 1.69-1.57 (m, 2H), 1.17 (t, J=7.6 Hz, 3H); APCI MS m/z 339 [M+H]+.

後処理

  1. temperatureAfter this time, the mixture was cooled
  2. filtrationfiltered
  3. washthrough celite washing with ethyl acetate
  4. washThe filtrate was washed with brine (3×15 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (silica, hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-aefce0809de5472a981ee36f0c4dc55a
出典データセット
uspto-grants-2015_12
特許番号
US09221843B2

反応ノート

読み込み中…