3,4,5-Trimethoxyaniline → HCID 11957393, compound

HRID 2426280Notes

Reaction equation

HRID 2426280 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[CH:9][N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[C:6]=2[N:7]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[NH2:22].CC(C)([O-])C.[K+]>O1CCOCC1>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:8]1[C:6]2[N:7]=[C:2]([NH:22][C:21]3[CH:23]=[C:24]([O:28][CH3:29])[C:25]([O:26][CH3:27])=[C:19]([O:18][CH3:17])[CH:20]=3)[N:3]=[CH:4][C:5]=2[CH:10]=[CH:9]1

Participants

5

Reactant 3

HCID 322853,4,5-TrimethoxyanilineHCID 23665647Potassium tert-butoxideHCID 58973801HCID 58973801, compound

Product 1

HCID 11957393HCID 11957393, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-7-pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidine in 1,4-dioxane is added 3,4,5-trimethoxy aniline (3 equivalents) followed by adding potassium tert-butoxide solution (1.0 M in tetrahydrofuran, 3 equivalents) dropwise. After addition, the reaction mixture is heated at 80° C. for 2 hours. The solvent is removed after cooling to room temperature. Purification by reverse phase HPLC gives (7-pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-(3,4,5-trimethoxy-phenyl)-amine as a white solid.

Workup

  1. additionAfter addition
  2. customThe solvent is removed
  3. temperatureafter cooling to room temperature
  4. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-bb5c9bcbed564a29a34fdb0504e4430c
Source dataset
uspto-grants-2011_06
Patent number
US07968557B2

Reaction notes

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