Triethylamine → HCID 59686869, 화합물

HRID 426149노트

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HRID 426149 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([CH2:11]O)[CH:8]=[CH:7][N:6]=1)=[O:4].C([N:15]([CH2:18][CH3:19])CC)C.CS(Cl)(=O)=O.[CH:25]([C:28]1[C:33](=[O:34])[NH:32][C:31](=[O:35])[NH:30][C:29]=1OC1C=C(C=C(C)C=1)C#N)([CH3:27])[CH3:26].[C:46](=[O:49])([O-])[O-].[K+].[K+].[I-].[Li+]>C(Cl)(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([CH2:11][N:30]2[C:29]([C:46](=[O:49])[C:5]3[CH:10]=[C:9]([CH3:11])[CH:8]=[C:19]([C:18]#[N:15])[CH:3]=3)=[C:28]([CH:25]([CH3:26])[CH3:27])[C:33](=[O:34])[NH:32][C:31]2=[O:35])[CH:8]=[CH:7][N:6]=1)=[O:4]

참가 물질

9

반응물 6

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 66321Lithium iodideHCID 23093785Methyl 4-(hydroxymethyl)pyridine-2-carboxylateHCID 596868373-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzonitrile

생성물 1

HCID 59686869HCID 59686869, 화합물수율 93.4%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 2-methoxycarbonylpyridine-4-methanol (222 mg, 1.3 mmol) in chloroform (10 ml) cooled in an ice bath under nitrogen atmosphere, was added triethylamine (279 μl, 2 mmol) and methanesulfonyl chloride (120 μl, 1.5 mmol) was added dropwise. After stirring for 1.1 hr., the reaction mixture was washed with saturated aqueous sodium bicarbonate, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was further dried in high vacuo for ca. 20 min. and mixed with (73) (394 mg, 1.3 mmol), powdered anhydrous potassium carbonate (183 mg, 1.3 mmol), and lithium iodide (178 mg, 1.3 mmol). DMF (7 ml) was then added to the mixture at room temperature and stirred for overnight. After evaporation of DMF, the residue was dissolved in methanol-chloroform (1:9) and filtered through celite pad. The filtrate was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (4:1)) to afford 271 mg (45%) of a white foam. 1H-NMR (200 MHz, CDCl3) δ 1.13 (3H, d, J=6.8 Hz), 1.23 (3H, d, J=6.8 Hz), 2.23 (1H, m), 2.37 (3H, s), 4.00 (3H, s), 4.66 (1H, d, J=17.0 Hz), 5.11 (1H, d, J=17.0 Hz), 7.23 (1H, m), 7.65 (2H, s), 7.73 (1H, s), 7.88 (1H, s), 8.55 (1H, d, J=5.2 Hz), 9.56 (1H, s).

후처리

  1. additionwas added dropwise
  2. wash, the reaction mixture was washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was further dried in high vacuo for ca. 20 min.
  7. stirringstirred for overnight
  8. customAfter evaporation of DMF
  9. dissolutionthe residue was dissolved in methanol-chloroform (1:9)
  10. filtrationfiltered through celite pad
  11. customThe filtrate was then evaporated in vacuo
  12. customthe residue was purified by silica gel column chromatography (eluent, EA:hexanes (4:1))

출처 및 근거

ORD 기록
ord-334bd6a7f9024c8e871f9b4fce3e491d
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106064B2

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