Sodium Methoxide → 2-Butyl-5,6,7,8-tetrahydro-6-(2-hydroxy-2-methyl-1-oxopropyl)-pyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1198464

반응식

HRID 1198464 반응식
[OH:1][C:2]([CH3:18])([CH3:17])[C:3]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH:7]([C:12]([O:14]CC)=O)[CH2:6]1)=[O:4].Cl.[C:20]([NH2:26])(=[NH:25])[CH2:21][CH2:22][CH2:23][CH3:24].C[O-].[Na+]>C(O)C.CO.CC(C)=O>[CH2:21]([C:20]1[NH:26][C:12](=[O:14])[C:7]2[CH2:6][N:5]([C:3](=[O:4])[C:2]([OH:1])([CH3:17])[CH3:18])[CH2:10][CH2:9][C:8]=2[N:25]=1)[CH2:22][CH2:23][CH3:24]

참가 물질

7

반응물 3

HCID 10942334Sodium MethoxideHCID 11615174Pentanimidamide HydrochlorideHCID 19102679HCID 19102679, 화합물

생성물 1

HCID 1356749692-Butyl-5,6,7,8-tetrahydro-6-(2-hydroxy-2-methyl-1-oxopropyl)-pyrido[4,3-d]pyrimidin-4(3H)-one수율 81.4%

시약·촉매·용매 3

HCID 180Acetone용매HCID 702Ethanol용매HCID 887Methanol용매

실험 절차

A mixture of 0.7 g of ethyl 1-(2-hydroxy-2-methyl-1-oxopropyl)-4-oxo-3-piperidinecarboxylate and 0.4 g of valeramidine hydrochloride in 8 ml of anhydrous ethyl alcohol is treated with 2.8 ml of a 1M solution of sodium methoxide in methanol. The resulting mixture is stirred and heated at reflux for one hour. The reaction mixture is allowed to cool over 30 minutes then filtered. The filtrate is evaporated to a syrup which is stirred with 50 ml of ether overnight. The ether is decanted to afford a oily solid which is dissolved in acetone and applied to thick layer silica gel plates. The plates are eluted with ethyl acetate and the major zone washed stirred with water and the water decanted. The residue is dried and chromatographed on thick layer silica gel chromatography plates using ethyl acetate as the elution solvent. The major band at Rf=0.2 is isolated by washing with acetone to afford 0.65 g of the desired product as a colorless solid, m.p. 159°-161° C.

후처리

  1. temperatureheated
  2. temperatureat reflux for one hour
  3. temperatureto cool over 30 minutes
  4. filtrationthen filtered
  5. customThe filtrate is evaporated to a syrup which
  6. stirringis stirred with 50 ml of ether overnight
  7. customThe ether is decanted
  8. customto afford a oily solid which
  9. washThe plates are eluted with ethyl acetate
  10. washthe major zone washed
  11. stirringstirred with water
  12. customthe water decanted
  13. customThe residue is dried
  14. customchromatographed on thick layer silica gel chromatography plates
  15. customThe major band at Rf=0.2 is isolated
  16. washby washing with acetone

출처 및 근거

ORD 기록
ord-1fe5d88bb3154b16b4e530621125448c
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05281602

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