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

HRID 1774434

反応式

HRID 1774434 の反応式
[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

参加物

7

反応物 4

HCID 6497Dimethyl SulfateHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 178517543HCID 178517543、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-086b44e91feb448a967a1afc2173fc05
出典データセット
uspto-grants-2016_02
特許番号
US09260413B2

関連ノート

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