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Sodium Hydroxide → 6-(5-chloro-6-methoxy-3-pyridinyl)-1,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-one

HRID 242314
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HRID 242314 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:21][CH2:20][C:13]3[N:14]=[CH:15][N:16]=[C:17]([O:18]C)[C:12]=3[CH2:11]2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:21][CH2:20][C:13]3[N:14]=[CH:15][N:16]=[C:17]([OH:18])[C:12]=3[CH2:11]2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9]
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참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 574953156-(5-Chloro-6-methoxy-pyridin-3-yl)-4-methoxy-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine2회

생성물 1

HCID 1784942106-(5-chloro-6-methoxy-3-pyridinyl)-1,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-one수율 107%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
90 °C

실험 절차

To 6-(5-chloro-6-methoxy-pyridin-3-yl)-4-methoxy-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine (intermediate 15)(95 mg, 0.31 mmol) in MeOH (5.0 mL) in a glass vial was added 2M NaOH(aq) (3.0 mL). The vial was capped and heated at 90° C. for 24 h. Acidified with glacial AcOH to pH 6, evaporated in vacuo and the residue extracted with CH2Cl2 (1×50 mL with stirring). With each extraction, the CH2Cl2 layer was decanted from the solid residue. The CH2Cl2 layers were combined. The solid residue was then washed with water (10 mL) and filtered. This filtered solid was combined with the CH2Cl2 layers and evaporated in vacuo to give 6-(5-chloro-6-methoxy-pyridin-3-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-ol as a yellow solid (90 mg, 107% yield) LCMS: [M+H]+=293.0/294.8, Rt(3)=1.38 min.

후처리

  1. customThe vial was capped
  2. customAcidified with glacial AcOH to pH 6, evaporated in vacuo
  3. extractionthe residue extracted with CH2Cl2 (1×50 mL with stirring)
  4. extractionWith each extraction
  5. customthe CH2Cl2 layer was decanted from the solid residue
  6. washThe solid residue was then washed with water (10 mL)
  7. filtrationfiltered
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-0adb5dbcfc28475485aad3147fdc7aa6
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08653092B2

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