Dimethylformamide → HCID 57990338, compound

HRID 2281509Notes

Reaction equation

HRID 2281509 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:5]2[C:10](I)=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1.[CH3:31][N:32](C=O)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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.[Fe+2].[C-]#N.[C-]#N.[Zn+2]>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:5]2[C:10]([C:31]#[N:32])=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 57990348HCID 57990348, compound

Product 1

HCID 57990338HCID 57990338, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
70 °C

Procedure

A solution of 2-chloro-5-iodo-N-(4-methoxyphenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (257 mg, 0.463 mmol), Pd2 dba3 (25 mg, 0.027 mmol) and dppf (51 mg, 0.092 mmol) in DMF (4 mL) was degassed with argon before being charged with Zn(CN)2 (65 mg, 0.555 mmol). The mixture was stirred at 70° C. for 3 h. DMF was removed in vacuo. The residue was dissolved in CH3CN. Water was added to induce precipitation. The precipitate was collected and dried on vacuum to give 2-chloro-4-(4-methoxyphenylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (68 mg).

Workup

  1. customDMF was removed in vacuo
  2. dissolutionThe residue was dissolved in CH3CN
  3. additionWater was added
  4. customprecipitation
  5. customThe precipitate was collected
  6. customdried on vacuum

Sources & evidence

ORD record
ord-6309aa571c314b808577fcc23280d31a
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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