Dimethyl Sulfate → 5-(benzyloxy)-2-(2-chloropyridin-4-yl)-3-methylpyrimidin-4(3H)-one

HRID 869303

반응식

HRID 869303 반응식
[CH2:1]([O:8][C:9]1[C:10]([OH:22])=[N:11][C:12]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[CH:16]=2)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O-])([O-])=O.[Cs+].[Cs+].COS(OC)(=O)=O.CCOC(C)=O>O1CCOCC1.O>[CH2:1]([O:8][C:9]1[C:10](=[O:22])[N:11]([CH3:23])[C:12]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[CH:16]=2)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 6497Dimethyl SulfateHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 178517543HCID 178517543, 화합물

생성물 1

HCID 772309535-(benzyloxy)-2-(2-chloropyridin-4-yl)-3-methylpyrimidin-4(3H)-one수율 22%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a mixture of 5-(benzyloxy)-2-(2-chloropyridin-4-yl)pyrimidin-4-ol (14.2 g, 112 mmol), Cs2CO3 (36.6 g, 112 mmol) in 300 mL of 1,4-dioxane, was added Me2SO4 (17.6 g, 56 mmol) and the resulting mixture was refluxed for 5 min. After cooling to rt, EtOAc (300 mL) and water (200 mL) were added. The organic layer was separated, the aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layer was washed with water, brine, and dried over Mg2SO4, filtered, and concentrated to give 25 g of crude compound, which was purified by silica gel to afford 5-(benzyloxy)-2-(2-chloropyridin-4-yl)-3-methylpyrimidin-4(3H)-one (4.0 g, 22%). 1H-NMR δ (400 MHz, d6-DMSO): 8.53 (dd, J=5.2, 0.4 Hz, 1H), 7.51 (s, 1H), 7.44 (m, 3H), 7.42-7.29 (m, 4H), 5.19 (s, 2H), 3.33 (s, 3H); MS (ESI) m/z (M+H)+ 328.

후처리

  1. temperaturethe resulting mixture was refluxed for 5 min
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give 25 g of crude compound, which
  9. customwas purified by silica gel

출처 및 근거

ORD 기록
ord-6bbdcce83b484b4cb10a0c20aaf72f35
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969364B2

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