Potassium Iodide → 4-{4-[2-(2,2,6,6-Tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-phenyl}-butyronitrile

HRID 1435007Notes

Reaction equation

HRID 1435007 reaction equation
[CH3:1][C:2]1([CH3:37])[CH2:7][CH:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22]COS(C4C=CC(C)=CC=4)(=O)=O)=[CH:17][CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH2:5][C:4]([CH3:36])([CH3:35])[NH:3]1.[C-]#[N:39].[K+].[I-].[K+].CCO[C:46]([CH3:48])=O>CS(C)=O>[CH3:37][C:2]1([CH3:1])[CH2:7][CH:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:48][C:46]#[N:39])=[CH:17][CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH2:5][C:4]([CH3:35])([CH3:36])[NH:3]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 57936242Toluene-4-sulfonic acid 3-{4-[2-(2,2,6,6-tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-phenyl}-propyl ester

Product 1

HCID 579362134-{4-[2-(2,2,6,6-Tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-phenyl}-butyronitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of toluene-4-sulfonic acid 3-{4-[2-(2,2,6,6-tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-phenyl}-propyl ester (80 mg, 0.15 mmol), (Step A of Example 190), KCN (20 mg, 0.31 mmol) and a catalytic amount of potassium iodide in 2 ml DMSO was stirred for 2 hours at 100° C. The reaction mixture was diluted with EtOAc and washed with water. The crude product was purified using preparative TLC. Yield: 9 mg (16%).

Workup

  1. washwashed with water
  2. customThe crude product was purified

Sources & evidence

ORD record
ord-8440f411ab6b4393911fe7bf20078d83
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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