Thionyl Chloride → Benzo[1,3]dioxol-5-yl-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

HRID 133044Notes

Reaction equation

HRID 133044 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]3[C:12]4[CH:19]=[C:18]([C:20]5[CH:25]=[CH:24][C:23]([CH2:26]O)=[CH:22][CH:21]=5)[NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.S(Cl)([Cl:30])=O>O1CCOCC1.C(#N)C.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]3[C:12]4[CH:19]=[C:18]([C:20]5[CH:25]=[CH:24][C:23]([CH2:26][Cl:30])=[CH:22][CH:21]=5)[NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 69180666{4-[4-(Benzo[1,3]dioxol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

Product 1

HCID 69179724Benzo[1,3]dioxol-5-yl-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolventHCID 22504236Acetonitrile dioxaneSolvent

Procedure

To a suspension of 1.83 g of {4-[4-(benzo[1,3]dioxol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol in 56 ml of dioxane/acetonitrile 1:1 under N2-atmosphere, 3.1 ml of thionylchloride are added. After 16 h stirring, the suspension is diluted with ethyl acetate and NaHCO3-solution. The aqueous layer is separated off and extracted twice with ethyl acetate. The organic phases are washed with water and brine, dried (MgSO4) and concentrated to yield the title compound; MS-ES+: (M+H)+=379; HPLC (conditions see Examples 67-78) tR =11.4 min.

Workup

  1. customThe aqueous layer is separated off
  2. extractionextracted twice with ethyl acetate
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5fad3f3dd67047459c67a329021f6ed5
Source dataset
uspto-grants-2008_06
Patent number
US07390805B2

Reaction notes

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