1,2-Diaminocyclohexane, trans- → 2-Chloro-7-(4-methanesulfonyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1966393Notes

Reaction equation

HRID 1966393 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.BrC1C=CC([CH2:18][S:19](CC2C=CC(Br)=CC=2)(=[O:21])=[O:20])=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].N[C@@H:39]1[CH2:44][CH2:43][CH2:42][CH2:41][C@H:40]1N>O1CCOCC1.[Cu]I>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[CH:9][N:8]([C:43]3[CH:42]=[CH:41][C:40]([S:19]([CH3:18])(=[O:21])=[O:20])=[CH:39][CH:44]=3)[C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 2674191,1'-[Sulfonylbis(methylene)]bis(4-bromobenzene)HCID 57067742-Chloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 452575582-Chloro-7-(4-methanesulfonyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

In a seal tube, 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (600 mg, 3.56 mmol), 4-bromophenylmethylsulfone (700 mg, 4.10 mmol), CuI (239 mg, 1.23 mmol), and K3PO4 (2.67 g, 12.3 mmol) are suspended in 1,4-dioxane (30 mL). Then, trans-1,2-diaminocyclohexane (149 μL, 1.23 mmol) is added at rt. The reaction vial is flushed with Ar and the mixture is heated to 110° C. for 3 h. After cooling to rt, the reaction mixture is concentrated under reduce pressure. The residue is suspended in EtOAc and washed with saturated aqueous NaCl solution (3×). The organic layer is dried over MgSO4, filtered, and concentrated under reduced pressure. The solid residue is triturated with small amounts of EtOAc to yield the title compound as a brown solid.

Workup

  1. customThe reaction
  2. customvial is flushed with Ar
  3. temperatureAfter cooling to rt
  4. concentrationthe reaction mixture is concentrated
  5. washwashed with saturated aqueous NaCl solution (3×)
  6. dry with materialThe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe solid residue is triturated with small amounts of EtOAc

Sources & evidence

ORD record
ord-4913325d500641f596b4bdf634a9a43a
Source dataset
uspto-grants-2013_04
Patent number
US08420657B2

Reaction notes

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