Azobisisobutyronitrile → HCID 178508720, compound

HRID 1968622Notes

Reaction equation

HRID 1968622 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[N:8][C:9]([NH2:10])=[C:4]2[CH:3]=[N:2]1.IN1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:39][C:40]1[CH:53]=[C:52](B2OC(C)(C)C(C)(C)O2)[CH:51]=[CH:50][C:41]=1[O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1>C(#N)C.CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:39][C:40]1[CH:53]=[C:52]([C:3]2[C:4]3[C:5](=[N:6][CH:7]=[N:8][C:9]=3[NH2:10])[NH:1][N:2]=2)[CH:51]=[CH:50][C:41]=1[O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1

Participants

9

Reactant 5

HCID 6547AzobisisobutyronitrileHCID 62657Potassium Phosphate, TribasicHCID 754201H-Pyrazolo[3,4-d]pyrimidin-4-amineHCID 120273N-IodosuccinimideHCID 59361775HCID 59361775, compound

Product 1

HCID 178508720HCID 178508720, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

1H-pyrazolo[3,4-d]pyrimidin-4-amine (1 equivalent), N-iodosuccinimide (1.25 equivalents) and AIBN (0.1 equivalents) are heated in acetonitrile for 10 h. The reaction is filtered and the filtered material (1 equivalent) is placed in DMF. Pd(dppf)Cl2 (0.6 equivalents), KI (0.1 equivalents), K3PO4 (3 equivalents) and 2-((2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)methyl)pyridine (1 equivalent) are added and the mixture is heated at 80° C. overnight. The reaction is partitioned between EtOAc and water, the organic layer is separated, washed with water, brine, dried over Na2SO4 and filtered. The filtrate is concentrated under reduced pressure and purified by column chromatography.

Workup

  1. filtrationThe reaction is filtered
  2. customThe reaction is partitioned between EtOAc and water
  3. customthe organic layer is separated
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-8558f0f30e7342a28578d9f738ad7640
Source dataset
uspto-grants-2013_04
Patent number
US08426428B2

Reaction notes

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