Cesium carbonate → N-(5-(4-methylpiperazin-1-yl)piridin-2-yl)-4-(3-nitrophenoxy)thieno[3,2-d]pyrimidin-2-amine

HRID 1850019ノート

反応式

HRID 1850019 の反応式
Cl[C:2]1[N:3]=[C:4]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[CH:30][C:31]([NH2:34])=[N:32][CH:33]=2)[CH2:24][CH2:23]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[CH:30][C:31]([NH:34][C:2]3[N:3]=[C:4]([O:11][C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=4)[C:5]4[S:10][CH:9]=[CH:8][C:6]=4[N:7]=3)=[N:32][CH:33]=2)[CH2:24][CH2:23]1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 223298335-(4-Methylpiperazin-1-yl)pyridin-2-amineHCID 866828282-Chloro-4-(3-nitrophenoxy)thieno[3,2-d]pyrimidine

生成物 1

HCID 89542484N-(5-(4-methylpiperazin-1-yl)piridin-2-yl)-4-(3-nitrophenoxy)thieno[3,2-d]pyrimidin-2-amine収率 70.1%

試薬・触媒・溶媒 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

0.6 g (1.94 mmol) of the compound obtained in Step 3 of Example 1 and 0.75 g (3.88 mmol) of 5-(4-methylpiperazin-1-yl)piridin-2-amine were dissolved in 8 ml of 1,4-dioxane, and 178 mg (0.2 mmol) of tris(dibenzylideneacetone)dipalladium(O) and 122 mg (0.2 mmol) of 2,2′-bis(diphenylphosphino)-1,1′-binaphthy were added thereto, and stirred for 5 minutes at room temperature. 1.27 g (3.88 mmol) of cesium carbonate was added thereto, and stirred for 3 hours at 100° C. Upon the completion of the reaction, the resulting mixture was cooled to room temperature and filtered over a short bed of Celite filter, and diluted with dichloromethane and washed with water. The organic layer was separated, dried over anhydrous Na2SO4, and filtered and distilled under a reduced pressure. The resulting residue was separated by column chromatography (dichloromethane:methanol (20:1, v/v)) to obtain 630 mg of the title compound (yield: 70%).

後処理

  1. stirringstirred for 3 hours at 100° C
  2. customUpon the completion of the reaction
  3. temperaturethe resulting mixture was cooled to room temperature
  4. filtrationfiltered over a short bed of Celite
  5. filtrationfilter
  6. additiondiluted with dichloromethane
  7. washwashed with water
  8. customThe organic layer was separated
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered
  11. distillationdistilled under a reduced pressure
  12. customThe resulting residue was separated by column chromatography (dichloromethane:methanol (20:1

出典と根拠

ORDレコード
ord-7f2644607c044be8a49a4bf51c010e22
出典データセット
uspto-grants-2015_02
特許番号
US08957065B2

反応ノート

読み込み中…