Thionyl Chloride → (2-Methoxy-pyridin-4-yl)-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

HRID 1295664Notes

Reaction equation

HRID 1295664 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH:9][C:10]2[C:11]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([CH2:25]O)=[CH:21][CH:20]=4)[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:6]=[CH:5][N:4]=1.O=S(Cl)[Cl:29]>C(#N)C.O1CCOCC1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH:9][C:10]2[C:11]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([CH2:25][Cl:29])=[CH:21][CH:20]=4)[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 2

HCID 24386Thionyl ChlorideHCID 69180544{4-[4-(2-methoxy-pyridin-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

Product 1

HCID 69182275(2-Methoxy-pyridin-4-yl)-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

Reagents, catalysts & solvents 4

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

At 0° C., a suspension of 1.23 g (3.5 mMol) of {4-[4-(2-methoxy-pyridin-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol in 18 ml of acetonitrile, 18 ml of dioxane and 1.5 ml of SOCl2 is prepared at 0° C. and then stirred for 4.5 h at RT. The mixture is diluted with 0.2 I of EtOAc and 0.1 I of saturated NaHCO3-solution, stirred and the title compound filtered off; MS-ES+: (M+H)+=366. More product can be obtained by extraction of the filtrate.

Workup

  1. customis prepared at 0° C.
  2. stirringstirred
  3. filtrationthe title compound filtered off
  4. customMore product can be obtained by extraction of the filtrate

Sources & evidence

ORD record
ord-b953aa4a7f304d45af5fefaba687533d
Source dataset
uspto-grants-2007_07
Patent number
US07244729B2

Reaction notes

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