Iodine → HCID 71746453、化合物

HRID 570546ノート

反応式

HRID 570546 の反応式
N[C:2]1[C:3]2[C:26]([CH3:28])([CH3:27])[C:25](=[O:29])[NH:24][C:4]=2[N:5]=[C:6]([C:8]2[C:9]3[CH2:23][CH2:22][CH2:21][C:10]=3[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[N:12]=2)[N:7]=1.N(OCCC(C)C)=O.[I:38]I.[I-].[Cs+]>C(COC)OC.[Cu]I>[F:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][N:11]1[C:10]2[CH2:21][CH2:22][CH2:23][C:9]=2[C:8]([C:6]2[N:7]=[C:2]([I:38])[C:3]3[C:26]([CH3:27])([CH3:28])[C:25](=[O:29])[NH:24][C:4]=3[N:5]=2)=[N:12]1

参加物

7

反応物 4

HCID 807IodineHCID 8053Isoamyl NitriteHCID 24601Cesium iodideHCID 712856274-Amino-2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

生成物 1

HCID 71746453HCID 71746453、化合物

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
100 °C

実験手順

285 mg (0.68 mmol) of 4-amino-2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one were initially charged in absolute dimethoxyethane, and 800 mg (6.83 mmol) of isopentyl nitrite, 87 mg (0.34 mmol) of iodine, 39 mg (0.21 mmol) of copper(I) iodide and 177 mg (0.68 mmol) of caesium iodide were added. The mixture was stirred at 100° C. for 40 min. The mixture was concentrated on a rotary evaporator, and the residue was taken up in dichloromethane and washed with 5% aqueous sodium thiosulphate solution and saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate, concentrated and purified by means of preparative HPLC (eluent: acetonitrile/water with 0.1% acetic acid, gradient 20:80→100:0). 148 mg (40% of theory) of the target compound were obtained.

後処理

  1. concentrationThe mixture was concentrated on a rotary evaporator
  2. washwashed with 5% aqueous sodium thiosulphate solution and saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated
  5. custompurified by means of preparative HPLC (eluent: acetonitrile/water with 0.1% acetic acid, gradient 20:80→100:0)
  6. custom148 mg (40% of theory) of the target compound were obtained

出典と根拠

ORDレコード
ord-7d96a6c9ccad4a70a41a8454a5dfd1c3
出典データセット
uspto-grants-2015_05
特許番号
US09023849B2

反応ノート

読み込み中…