Potassium Iodide → Benzyl 3-{3-[1-(4-amino-5-oxopyrido[2,3-d]pyrimidin-8(5H)-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl}azetidine-1-carboxylate

HRID 1499719ノート

反応式

HRID 1499719 の反応式
[NH2:1][C:2]1[C:3]2[C:11](=[O:12])[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[Cl:21][C:22]1[C:23]([CH3:48])=[C:24]([CH:34]2[CH2:37][N:36]([C:38]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:39])[CH2:35]2)[C:25]([O:31][CH2:32][CH3:33])=[C:26]([CH:28](Cl)[CH3:29])[CH:27]=1>CN(C)C=O.O>[NH2:1][C:2]1[C:3]2[C:11](=[O:12])[CH:10]=[CH:9][N:8]([CH:28]([C:26]3[C:25]([O:31][CH2:32][CH3:33])=[C:24]([CH:34]4[CH2:37][N:36]([C:38]([O:40][CH2:41][C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=5)=[O:39])[CH2:35]4)[C:23]([CH3:48])=[C:22]([Cl:21])[CH:27]=3)[CH3:29])[C:4]=2[N:5]=[CH:6][N:7]=1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 57067884-aminopyrido[2,3-d]pyrimidin-5(8H)-oneHCID 86677655HCID 86677655、化合物

生成物 1

HCID 86677657Benzyl 3-{3-[1-(4-amino-5-oxopyrido[2,3-d]pyrimidin-8(5H)-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl}azetidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

To a mixture of 4-aminopyrido[2,3-d]pyrimidin-5(8H)-one (11.5 mg, 0.0708 mmol), cesium carbonate (34 mg, 0.10 mmol) and potassium iodide (1.2 mg, 0.0071 mmol) in N,N-dimethylformamide (0.2 mL) was added benzyl 3-[3-chloro-5-(1-chloroethyl)-6-ethoxy-2-methylphenyl]azetidine-1-carboxylate (30 mg, 0.07 mmol). The mixture was stirred at 140° C. for 1 hour, cooled and then diluted with water, extracted with ether. The combined organic layers were dried over MgSO4 and concentrated to afford the crude product which was used in the next step directly. LCMS calculated for C29H31ClN5O4 (M+H)+: m/z=548.2; Found: 548.2.

後処理

  1. temperaturecooled
  2. extractionextracted with ether
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-de5701c0f65748f58f30b861baef921f
出典データセット
uspto-grants-2015_12
特許番号
US09199982B2

反応ノート

読み込み中…