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

HRID 241557

반응식

HRID 241557 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-03b7fd8909164bc2bac911665a874d1e
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653059B2

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