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Potassium Carbonate → tert-butyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(2-(tetrahydrofuran-2-yl)ethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1930723
ノート
印刷プレビュー

反応式

HRID 1930723 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][CH2:35][CH:36]1[CH2:40][CH2:39][CH2:38][O:37]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:18]=[C:33]([CH2:34][CH2:35][CH:36]3[CH2:40][CH2:39][CH2:38][O:37]3)[C:21]3[CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])[CH2:24][CH2:25][C:20]=3[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1
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

5

反応物 3

HCID 11430Potassium CarbonateHCID 59333690Tert-butyl 4-oxo-3-(3-(tetrahydrofuran-2-yl)propanoyl)piperidine-1-carboxylateHCID 178493227HCID 178493227、化合物

生成物 1

HCID 59333773tert-butyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(2-(tetrahydrofuran-2-yl)ethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate収率 28.9%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

反応条件

温度
60 °C

実験手順

A reaction mixture of 1-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (0.800 g, 2.17 mmol), tert-butyl 4-oxo-3-(3-(tetrahydrofuran-2-yl)propanoyl)piperidine-1-carboxylate (0.705 g, 2.17 mmol) and potassium carbonate (0.599 g, 4.33 mmol) in ethanol (6 mL) was stirred at 60° C. overnight. The reaction mixture was transferred to a microwave vial (20 mL) and run in the microwave at 120° C. for 45 minutes. The reaction mixture was filtered and washed with dichloromethane. The filtrate was concentrated and the residue was dissolved in dichloromethane and washed with water, dried (MgSO4) and concentrated. The crude product was purified by silica flash chromatography using a gradient of methanol in dichloromethane (0 to 4%) giving tert-butyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(2-(tetrahydrofuran-2-yl)ethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.335 g, 28.9%) as the product.

後処理

  1. waitrun in the microwave at 120° C. for 45 minutes
  2. filtrationThe reaction mixture was filtered
  3. washwashed with dichloromethane
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe crude product was purified by silica flash chromatography

出典と根拠

ORDレコード
ord-fdb27e4706544135b8223f8e6aa1c780
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08188101B2

反応ノート

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