Cesium fluoride → 6-(5-(1-Ethoxyvinyl)-2-fluoropyridin-3-yl)-2-methylpyrimidin-4-amine

HRID 1812384ノート

反応式

HRID 1812384 の反応式
Cl[C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH2:16])[CH:10]=2)[C:5]([F:8])=[N:6][CH:7]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[F-].[Cs+].C([Sn](CCCC)(CCCC)[C:58]([O:60][CH2:61][CH3:62])=[CH2:59])CCC>O1CCOCC1.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:61]([O:60][C:58]([C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH2:16])[CH:10]=2)[C:5]([F:8])=[N:6][CH:7]=1)=[CH2:59])[CH3:62]

参加物

8

反応物 4

HCID 25953Cesium fluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 666002626-(5-Chloro-2-fluoropyridin-3-yl)-2-methylpyrimidin-4-amine

生成物 1

HCID 665999816-(5-(1-Ethoxyvinyl)-2-fluoropyridin-3-yl)-2-methylpyrimidin-4-amine収率 80%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

To a 5 mL microwave reaction tube was added 6-(5-chloro-2-fluoropyridin-3-yl)-2-methylpyrimidin-4-amine (227 mg, 0.95 mmol), palladium acetate (10 mg, 0.048 mmol), X-phos (40 mg, 0.09 mmol), cesium fluoride (433 mg, 2.85 mmol) and tributyl(1-ethoxyvinyl)stannane (0.45 mL, 1.33 mmol) in 1,4-dioxane (4 mL) and DMF (1 mL). The glass tube was sealed and heated in a microwave at 120° C. for 1 h. The reaction mixture was passed through a short path of neutral alumina column, eluted with 50 mL of DCM followed by 150 mL of EtOAc and 50 mL of 5% MeOH in EtOAc. The desired fractions were collected, concentrated to give 6-(5-(1-ethoxyvinyl)-2-fluoropyridin-3-yl)-2-methylpyrimidin-4-amine (208 mg, 80% yield) as an off white crystalline solid. m/z (ESI, positive ion) 275.1 (M+H)+.

後処理

  1. customThe glass tube was sealed
  2. washeluted with 50 mL of DCM
  3. customThe desired fractions were collected
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-25ae30a5d1834465840075dfbf20ba02
出典データセット
uspto-grants-2013_01
特許番号
US08362241B2

反応ノート

読み込み中…