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Sodium Carbonate → 2-(4-{2-(2,6-Dimethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-6-methylpyrimidin-4-yl}piperazin-1-yl)acetamide

HRID 1455762
ノート
印刷プレビュー

反応式

HRID 1455762 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH2:17])=[O:16])[CH2:10][CH2:9]2)[C:5]([CH2:18][O:19][C:20]2[CH:25]=[C:24]([CH:26]([CH3:28])[CH3:27])[CH:23]=[CH:22][C:21]=2[CH3:29])=[C:4]([CH3:30])[N:3]=1.[CH3:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:33]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH3:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:33]=1[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH2:17])=[O:16])[CH2:10][CH2:9]2)[C:5]([CH2:18][O:19][C:20]2[CH:25]=[C:24]([CH:26]([CH3:28])[CH3:27])[CH:23]=[CH:22][C:21]=2[CH3:29])=[C:4]([CH3:30])[N:3]=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

5

反応物 3

HCID 10340Sodium CarbonateHCID 5833222,6-Dimethylphenylboronic acidHCID 575315092-{4-[2-Chloro-5-(5-isopropyl-2-methyl-phenoxymethyl)-6-methyl-pyrimidin-4-yl]-piperazin-1-yl}-acetamide

生成物 1

HCID 575313962-(4-{2-(2,6-Dimethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-6-methylpyrimidin-4-yl}piperazin-1-yl)acetamide

試薬・触媒・溶媒 1

HCID 31275
1,4-Dioxane
溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-{4-[2-chloro-5-(5-isopropyl-2-methyl-phenoxymethyl)-6-methyl-pyrimidin-4-yl]-piperazin-1-yl}-acetamide (20 mg, 0.05 mmol), 2,6-dimethylphenylboronic acid (21 mg, 0.14 mmol) and 2 M sodium carbonate (0.14 mL, 0.28 mmol) in dioxane (1 mL) is degassed with bubbling argon for 20 min. Pd(PPh3)4 (2.9 mg, 5 mol %) is added and the reaction mixture is heated at 100° C. under nitrogen with magnetic stirring. After 18 h, the reaction mixture is partitioned between EtOAc (10 mL) and water (2 mL), the organic layer is separated, washed with brine (2 mL), dried over sodium sulfate, filtered and evaporated at reduced pressure to obtain a dark oil. Purification on silica gel (3% MeOH/CH2Cl2 0.1% NH4OH) provides the title compound as a colorless film. LC/MS (Method 3), M+H=502.3, Rt=2.43 min.; 1H NMR (CDCl3) δ=7.07-7.19 (m, 4H), 6.82 (m, 2H), 5.44 (br, s, 1H), 4.97 (s, 2H), 3.57 (br, s, 4H), 3.02 (s, 2H), 2.91 (m, 1H), 2.62 (m, 4H) 2.56 (s, 3H), 2.22 (s, 3H), 2.16 (s, 6H), 1.28 (d, 6H).

後処理

  1. customis degassed with bubbling argon for 20 min
  2. additionPd(PPh3)4 (2.9 mg, 5 mol %) is added
  3. customthe reaction mixture is partitioned between EtOAc (10 mL) and water (2 mL)
  4. customthe organic layer is separated
  5. washwashed with brine (2 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated at reduced pressure
  9. customto obtain a dark oil
  10. customPurification on silica gel (3% MeOH/CH2Cl2 0.1% NH4OH)

出典と根拠

ORDレコード
ord-0cb367f6dcc848f9b55d1505e4082928
出典データセット
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07482350B2

反応ノート

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