Carbonic acid-guanidine (1:1) → Ethyl-3-(2-amino-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)-benzoate

HRID 338675ノート

反応式

HRID 338675 の反応式
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:15][CH2:14][C:13](=O)[C:12](=[CH:17]N(C)C)[CH2:11]2)[CH:5]=1.[C:22](=O)(O)O.[NH2:26][C:27]([NH2:29])=[NH:28].O.O.O.C([O-])(=O)C.[Na+]>CCO>[CH2:1]([O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:15][CH2:14][C:13]3[N:28]=[C:27]([NH2:29])[N:26]=[CH:17][C:12]=3[CH2:11]2)[CH:5]=1)[CH3:22]

参加物

5

反応物 3

HCID 286947Carbonic acid-guanidine (1:1)HCID 23665404Sodium Acetate TrihydrateHCID 86695813Methyl-3-(3-dimethylaminomethylene-4-oxopiperidin-1-yl)benzoate

生成物 1

HCID 86695814Ethyl-3-(2-amino-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)-benzoate収率 49.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of methyl-3-(3-dimethylaminomethylene-4-oxopiperidin-1-yl)-benzoate (1.52 g, 5.27 mmol) in EtOH (100 mL) was treated with guanidine carbonate (3.80 g, 21.08 mmol), followed by addition of sodium acetate trihydrate (5.74 g, 42.16 mmol). The reaction mixture was refluxed for 15 hours and the solvent was removed in vacuo. The residue was partitioned between water and ethyl acetate and the mixture was vigorously stirred at ambient temperature for several minutes. The yellow, amorphous precipitate was collected, washed with water, ethyl acetate, and dried to give 776 mg of the title compound. The ethyl acetate layer was dried (MgSO4), filtered, and concentrated. The residue obtained was triturated with diethyl ether to give an additional 182 mg of the title compound (958 mg total, 61%).

後処理

  1. temperatureThe reaction mixture was refluxed for 15 hours
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between water and ethyl acetate
  4. customThe yellow, amorphous precipitate was collected
  5. washwashed with water, ethyl acetate
  6. customdried

出典と根拠

ORDレコード
ord-caa3d354eeda4931a502a03b9afb6a39
出典データセット
uspto-grants-2014_11
特許番号
US08889870B2

反応ノート

読み込み中…