N-[4-Chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-5-trimethylsilanylethynyl-7H-pyrrolo [2,3-d]pyrimidin-2-yl]-2,2-dimethyl-propionamide → 4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-5-((trimethylsilyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 417845Notes

Reaction equation

HRID 417845 reaction equation
[Cl:1][C:2]1[C:3]2[C:17]([C:18]#[C:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][N:15]([CH2:24][C:25]3[C:30]([CH3:31])=[C:29]([O:32][CH3:33])[C:28]([CH3:34])=[CH:27][N:26]=3)[C:4]=2[N:5]=[C:6]([NH:8]C(=O)C(C)(C)C)[N:7]=1>[Cl-].[Cl-].[Zn+2]>[Cl:1][C:2]1[C:3]2[C:17]([C:18]#[C:19][Si:20]([CH3:22])([CH3:23])[CH3:21])=[CH:16][N:15]([CH2:24][C:25]3[C:30]([CH3:31])=[C:29]([O:32][CH3:33])[C:28]([CH3:34])=[CH:27][N:26]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1

Participants

3

Reactant 1

HCID 57713844N-[4-Chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-5-trimethylsilanylethynyl-7H-pyrrolo [2,3-d]pyrimidin-2-yl]-2,2-dimethyl-propionamide

Product 1

HCID 577138584-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-5-((trimethylsilyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

The title compound was prepared by cleaving the pivaloyl protecting group of N-[4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-5-trimethylsilanylethynyl-7H-pyrrolo[2,3-d]pyrimidin -2-yl]-2,2-dimethyl-propionamide with ZnCl2 according to the General Procedure B. tR=6.56 min. 1H NMR (CDCl3) δ 8.22 (s, 1H), 7.11 (s, 1H), 5.30 (s, 2H), 5.09 (s, 2H), 3.75 (s, 3H), 2.26 (s, 3H), 2.18 (s, 3H), 0.24 (s, 9H).

Sources & evidence

ORD record
ord-2f0e56b99f684ad58443ab142cb08d98
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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