2-Chloro-7H-pyrrolo[2,3-d]pyrimidine → HCID 66614193, compound

HRID 510110

Reaction equation

HRID 510110 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[N:9][N:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:5]2=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[Sn](CCCC)(CCCC)CCCC)CCC.Cl[C:47]1[N:48]=[CH:49][C:50]2[CH:55]=[CH:54][NH:53][C:51]=2[N:52]=1>O1CCOCC1.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>[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:47]3[N:48]=[CH:49][C:50]4[CH:55]=[CH:54][NH:53][C:51]=4[N:52]=3)=[N:9][N:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 57067742-Chloro-7H-pyrrolo[2,3-d]pyrimidineHCID 580656025-fluoro-1-(2-fluorobenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridineHCID 178448238HCID 178448238, compound

Product 1

HCID 66614193HCID 66614193, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Under an argon atmosphere, 2.000 g (5.389 mmol) of the compound from example 24A were dissolved in 200 ml of 1,4-dioxane, and 9.378 g (16.167 mmol) of hexabutyldistannane were added. Added to the mixture were 2.000 g (1.731 mmol) of tetrakis(triphenylphosphine)palladium(0) and 0.910 g (5.928 mmol) of 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (described in Bioorg. Med. Chem. 17(19), 6926-6936; 2009). The mixture was heated to reflux for 60 h. After cooling, the reaction mixture was filtered through Celite and the filtrate was concentrated on a rotary evaporator. The residue was stirred successively with ethyl acetate, acetonitrile and dimethyl sulfoxide. Subsequently, the residue was dissolved in trifluoroacetic acid, and acetonitrile and water were added until slight turbidity. The mixture was filtered and the filtrate was concentrated on a rotary evaporator and the residue was dried under high vacuum. 161 mg (8% of theory) of the title compound were obtained.

Workup

  1. additionAdded to the mixture
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 60 h
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered through Celite
  6. concentrationthe filtrate was concentrated on a rotary evaporator
  7. dissolutionSubsequently, the residue was dissolved in trifluoroacetic acid
  8. additionacetonitrile and water were added until slight turbidity
  9. filtrationThe mixture was filtered
  10. concentrationthe filtrate was concentrated on a rotary evaporator
  11. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-764991be8e434bd8a4cf8f0ea7c7308d
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Linked notes

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