Methyl iodide → 2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-((1S)-3-methoxycyclohexyl)pyrimidin-4-amine

HRID 526960Notes

Reaction equation

HRID 526960 reaction equation
CI.[Cl:3][C:4]1[CH:5]=[C:6]2[C:12]([C:13]3[N:18]=[C:17]([NH:19][CH:20]4[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[CH2:21]4)[C:16]([F:27])=[CH:15][N:14]=3)=[CH:11][N:10]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:7]2=[N:8][CH:9]=1.Cl[C:39]1C=C2C(C3N=C(NC4CCC[C@H](O)C4)C(F)=CN=3)=CN(S(C3C=CC(C)=CC=3)(=O)=O)C2=NC=1.S([O-])([O-])(=O)=O.[Ca+2]>[Ag]=O>[Cl:3][C:4]1[CH:5]=[C:6]2[C:12]([C:13]3[N:18]=[C:17]([NH:19][C@H:20]4[CH2:25][CH2:24][CH2:23][CH:22]([O:26][CH3:39])[CH2:21]4)[C:16]([F:27])=[CH:15][N:14]=3)=[CH:11][N:10]([S:28]([C:31]3[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=3)(=[O:30])=[O:29])[C:7]2=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24497Calcium SulfateHCID 672851873-[[2-[5-Chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]-cyclohexanolHCID 68007634(S)-3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexanol

Product 1

HCID 680075682-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-((1S)-3-methoxycyclohexyl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 92152Silver(II) oxideCatalyst

Procedure

To a suspension of methyl iodide (0.20 g, 0.41 mmol) and 3-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]-cyclohexanol, 27a, (0.47 g, 2.04 mmol) was added silver oxide (0.578 g, 4.07 mmol and calcium sulfate (0.28 g, 2.04 (mmol). The reaction mixture was stirred at room temperature for 18 h. The mixture was filtered through celite and the resulting filtrate was concentrated in vacuo. The resulting crude mixture was purified by silica gel chromatography to afford 120 mg of the desired product, 27b.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe resulting filtrate was concentrated in vacuo
  3. customThe resulting crude mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e28d6c33d1e742c0a3c6419fa99feb83
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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