4-Chloro-5-iodo-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine → 4-chloro-5-(5-(4-ethylpiperazin-1-yl)pent-1-ynyl)-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 417862Notes

Reaction equation

HRID 417862 reaction equation
[Cl:1][C:2]1[C:3]2[C:11](I)=[CH:10][N:9]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1.[CH2:24]([N:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][CH2:34][C:35]#[CH:36])[CH2:28][CH2:27]1)[CH3:25]>>[Cl:1][C:2]1[C:3]2[C:11]([C:36]#[C:35][CH2:34][CH2:33][CH2:32][N:29]3[CH2:28][CH2:27][N:26]([CH2:24][CH3:25])[CH2:31][CH2:30]3)=[CH:10][N:9]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1

Participants

3

Reactant 2

HCID 442289644-Chloro-5-iodo-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amineHCID 866082201-Ethyl-4-(pent-4-ynyl)piperazine

Product 1

HCID 577138334-chloro-5-(5-(4-ethylpiperazin-1-yl)pent-1-ynyl)-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Procedure

Sonogashira coupling of 4-chloro-5-iodo-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo [2,3-d]pyrimidin-2-amine with 1-ethyl-4-(pent-4-ynyl)piperazine, according to the general procedure A gave the title compound, as a solid. Mp=142.3-144.1° C. HPLC Rt=4.11 min.

Sources & evidence

ORD record
ord-c8cb7366e24f46f0937dd8fb0dd25762
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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