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

HRID 1396541노트

반응식

HRID 1396541 반응식
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

참가 물질

8

반응물 3

HCID 10796Cesium carbonateHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 689626923-Bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine2회

생성물 1

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a2f4f180d8404f908258af1f3259f704
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901134B2

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