Sodium ethoxide → tert-Butyl 4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1930710ノート

反応式

HRID 1930710 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=[NH:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.O=[C:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH:21]1[C:33](=O)[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[O-]CC.[Na+]>C(O)C>[CH2:34]([C:33]1[C:21]2[CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25][C:20]=2[N:17]=[C:16]([NH:15][C:5]2[CH:6]=[CH:7][C:8]([N:9]3[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:18]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

参加物

5

反応物 3

HCID 2723922Sodium ethoxideHCID 59333761Tert-butyl 4-oxo-3-(2-phenylacetyl)piperidine-1-carboxylateHCID 178493227HCID 178493227、化合物

生成物 1

HCID 59333725tert-Butyl 4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate収率 92%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

1-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (300 mg, 1.22 mmol, example 43a), tert-butyl 4-oxo-3-(2-phenylacetyl)piperidine-1-carboxylate (466 mg, 1.47 mmol, example 41d) and sodium ethoxide (83 mg, 1.22 mmol) in ethanol (4 mL) were heated at 100° C. in a microwave reactor for 20 minutes. The reaction mixture was allowed to reach room temperature and the solvent was evaporated under reduced pressure. The crude was dissolved in ethyl acetate and washed with water. The organic phase was dried under MgSO4 and the solvent was evaporated under reduced pressure yielding tert-butyl 4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (590 mg, 92%) which was used in the subsequent step as such. MS (ES+) m/z 527.3 (M+H)+

後処理

  1. customto reach room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe crude was dissolved in ethyl acetate
  4. washwashed with water
  5. customThe organic phase was dried under MgSO4
  6. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-0a5a5da9c18b466ba64f8af44c1415ad
出典データセット
uspto-grants-2012_05
特許番号
US08188101B2

反応ノート

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