Formamidine acetate → tert-Butyl 7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 241557

反応式

HRID 241557 の反応式
C(O)(=O)C.[CH:5]([NH2:7])=[NH:6].[O-]CC.[Na+].O=[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C:14]1=[CH:26]N(C)C>C(O)C>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][C:13]2[N:6]=[CH:5][N:7]=[CH:26][C:14]=2[CH2:15]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

参加物

5

反応物 3

HCID 160693Formamidine acetateHCID 2723922Sodium ethoxideHCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

生成物 1

HCID 22707088tert-Butyl 7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

Formamidine acetate (472 mg, 4.52 mmol) in 15.0 mL of absolute ethanol was treated with sodium ethoxide (21 wt % solution in ethanol; 1.7 mL). After 30 min, a solution of the product from Step A above (1.15 g) in 8 mL of absolute ethanol was added, and the mixture was warmed at reflux for 18 h. The dark solution was cooled to room temperature and concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated to an orange oil. Purification by flash chromatography (silica gel; 2% methanol/dichloromethane as eluant) afforded the title compound as a light yellow gum.

後処理

  1. temperaturethe mixture was warmed
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated to an orange oil
  9. customPurification by flash chromatography (silica gel; 2% methanol/dichloromethane as eluant)

出典と根拠

ORDレコード
ord-03b7fd8909164bc2bac911665a874d1e
出典データセット
uspto-grants-2014_02
特許番号
US08653059B2

関連ノート

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