Ethyl Acetate → US9296747, Example 8

HRID 930506ノート

反応式

HRID 930506 の反応式
Cl[C:2]1[N:3]=[CH:4][C:5]2[CH2:11][N:10]([C:12]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[O:13])[CH2:9][CH2:8][C:6]=2[N:7]=1.[CH3:20][N:21]1[C:25]([NH2:26])=[CH:24][CH:23]=[N:22]1.CCOC(C)=O>C(O)(C)C>[CH3:20][N:21]1[C:25]([NH:26][C:2]2[N:3]=[CH:4][C:5]3[CH2:11][N:10]([C:12]([C:14]4[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=4)=[O:13])[CH2:9][CH2:8][C:6]=3[N:7]=2)=[CH:24][CH:23]=[N:22]1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 1369272-Methyl-2H-pyrazol-3-ylamineHCID 118970896(2-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)(pyridin-3-yl)methanone

生成物 1

HCID 118970898US9296747, Example 8収率 62.3%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
60 °C

実験手順

A solution of (2-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)(pyridin-3-yl)methanone, Intermediate 5 (0.025 g, 0.091 mmol) in isopropanol (0.1 mL) was treated with 1-methyl-1H-pyrazol-5-amine (0.010 g, 0.100 mmol). The resulting mixture was heated to 60° C. and allowed to stir overnight. After being allowed to cool to room temperature EtOAc (10 mL) was added to the reaction mixture, and the resulting solution was then washed twice with brine (10 mL). The combined aqueous layers were washed once with EtOAc (10 mL). The organic layers were combined, then dried over anhydrous Na2SO4(s), filtered and concentrated in vacuo. The resulting crude residue was then purified over silica using a MeOH/CHCl3 gradient. The desired product was obtained in 62.3% yield (0.019 g, 0.057 mmol).

後処理

  1. additionwas added to the reaction mixture
  2. washthe resulting solution was then washed twice with brine (10 mL)
  3. washThe combined aqueous layers were washed once with EtOAc (10 mL)
  4. dry with materialdried over anhydrous Na2SO4(s)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude residue was then purified over silica using a MeOH/CHCl3 gradient

出典と根拠

ORDレコード
ord-905e0443c245461abd010c552f585011
出典データセット
uspto-grants-2016_03
特許番号
US09296747B1

反応ノート

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