7-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridine → 5-(7-Chlorothieno[3,2-b]pyridin-2-yl)-1-(2-morpholinoethyl)pyrimidin-2(1H)-one

HRID 418740

반응식

HRID 418740 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([Sn](CCCC)(CCCC)CCCC)[S:10][C:3]=12.Br[C:25]1[CH:26]=[N:27][C:28](=[O:39])[N:29]([CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[CH:30]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:25]3[CH:26]=[N:27][C:28](=[O:39])[N:29]([CH2:31][CH2:32][N:33]4[CH2:34][CH2:35][O:36][CH2:37][CH2:38]4)[CH:30]=3)[S:10][C:3]=12

참가 물질

5

반응물 2

HCID 575166587-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridineHCID 587904085-Bromo-1-(2-morpholinoethyl)pyrimidin-2(1H)-one

생성물 1

HCID 587900885-(7-Chlorothieno[3,2-b]pyridin-2-yl)-1-(2-morpholinoethyl)pyrimidin-2(1H)-one수율 15.3%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To a solution of the tributyltin derivative 6 (1.88 g, 4.1 mmol) (scheme 2) in toluene (39 mL) was added 5-bromo-1-(2-morpholinoethyl)pyrimidin-2(1H)-one (413, 1.29 g, 4.5 mmol) and Pd(PPh3)4 (474 mg, 0.41 mmol). The reaction mixture was stirred at 100° C. for 16 h. The mixture was filtered and the solvent was evaporated. The residue was triturated in hexanes, then triturated in EtOAc to produce title compound 414 (236 mg, 15% yield). MS (m/z): 377.0 (M+H). 1H NMR (DMSO-d6) δ (ppm): 9.18 (d, J=3.5 Hz, 1H), 8.76 (d, J=3.3 Hz, 1H), 8.64 (d, J=5.1 Hz, 1H), 8.05 (s, 1H), 7.57 (d, J=5.1 Hz, 1H), 4.06 (t, J=5.9 Hz, 2H), 3.54 (t, J=4.5 Hz, 4H), 2.64 (t, J=5.9 Hz, 2H), 2.49-2.43 (m, 4H).

후처리

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated
  3. customThe residue was triturated in hexanes
  4. customtriturated in EtOAc

출처 및 근거

ORD 기록
ord-d76c378b771d43b2b6eb81dff81323c1
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093264B2

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