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Water → 5-Ethynyl-4-(4-methoxybenzyloxy)-2-(pyridin-2-yl)pyrimidine

HRID 1525339
ノート
印刷プレビュー

反応式

HRID 1525339 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:12]=[C:11]([OH:13])[C:10]([C:14]#[C:15][Si](C)(C)C)=[CH:9][N:8]=1.Cl[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.C(N(CC)CC)C.O>CN(C=O)C>[C:14]([C:10]1[C:11]([O:13][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[N:12][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:8][CH:9]=1)#[CH:15]
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

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 178504186HCID 178504186、化合物

生成物 1

HCID 894627915-Ethynyl-4-(4-methoxybenzyloxy)-2-(pyridin-2-yl)pyrimidine収率 25.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

反応条件

温度
80 °C

実験手順

A mixture of compound 37-i (1.0 g, 3.7 mmol), 1-(chloromethyl)-4-methoxybenzene (0.7 g, 4.4 mmol), and triethylamine (1.5 g, 11.1 mmol) in DMF (10 mL) was stirred overnight at 80° C. The reaction mixture was cooled to room temperature, poured into water, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (PE:EA=1:3) to afford compound 37-j (300 mg, 25%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.988-8.980 (s, 1H)), 8.775 (s, 1H), 8.581-8.555 (m, 1H), 8.020 (m, 1H), 7.554-7.541 (m, 1H), 7.522-7.493 (d, J=8.7 Hz, 2H), 6.924-6.895 (d, J=8.7 Hz, 2H), 5.741 (s, 2H), 3.807 (s, 1H), 3.509 (s, 1H), LC-MS (ESI): 318 [M+H]+

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (PE:EA=1:3)

出典と根拠

ORDレコード
ord-502ba185e92b42f4ad943ec00df9a7d0
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09079930B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート