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

HRID 1525339
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HRID 1525339 반응식
[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]
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참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 178504186HCID 178504186, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

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온도
80 °C

실험 절차

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]+

후처리

  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)

출처 및 근거

ORD 기록
ord-502ba185e92b42f4ad943ec00df9a7d0
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09079930B2

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