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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
ノート
印刷プレビュー

反応式

HRID 242314 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 574953156-(5-Chloro-6-methoxy-pyridin-3-yl)-4-methoxy-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0adb5dbcfc28475485aad3147fdc7aa6
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08653092B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート