Cesium carbonate → 3-(4-Benzyloxy-3-fluoro-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

HRID 1396541ノート

反応式

HRID 1396541 の反応式
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([NH2:11])=[N:8][CH:9]=2)[N:4]([CH3:12])[N:3]=1.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][C:22]=1[F:30])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[C:10]3[C:5](=[N:6][C:7]([NH2:11])=[N:8][CH:9]=3)[N:4]([CH3:12])[N:3]=2)=[CH:23][C:22]=1[F:30])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

8

反応物 3

HCID 10796Cesium carbonateHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 689626923-Bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine2 回

生成物 1

HCID 689679423-(4-Benzyloxy-3-fluoro-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

3-Bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (Intermediate 3) (0.33 g, 1.46 mmol) and 4-benzyloxy-3-fluoro phenylboronic acid (0.43 g, 1.75 mmol) are suspended in 1,4-dioxane (5 ml) in a microwave vial flushed with argon. A solution of Cs2CO3 (1.43 g, 4.38 mmol) in water (1.5 ml) is added followed by Pd(PPh3)4 (0.085 g, 0.073 mmol) and the reaction mixture is heated using microwave radiation at 150° C. for 0.5 hours. After cooling to room temperature the reaction mixture is diluted with EtOAc (100 ml) and washed with saturated NaHCO3. The organic portion is dried over MgSO4, filtered, concentrated in vacuo and the resulting crude solid is triturated with EtOAc (˜20 ml) to afford the title compound as an off-white solid.

後処理

  1. customvial flushed with argon
  2. temperaturethe reaction mixture is heated
  3. customat 150° C.
  4. customfor 0.5 hours
  5. washwashed with saturated NaHCO3
  6. dry with materialThe organic portion is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customthe resulting crude solid is triturated with EtOAc (˜20 ml)

出典と根拠

ORDレコード
ord-a2f4f180d8404f908258af1f3259f704
出典データセット
uspto-grants-2014_12
特許番号
US08901134B2

反応ノート

読み込み中…