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

HRID 417860Notes

Reaction equation

HRID 417860 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.[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][C:34]#[CH:35])[CH2:27][CH2:26]1>>[Cl:1][C:2]1[C:3]2[C:11]([C:35]#[C:34][CH2:33][CH2:32][CH2:31][N:28]3[CH2:27][CH2:26][N:25]([CH3:24])[CH2:30][CH2:29]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 234461161-Methyl-4-(pent-4-ynyl)piperazineHCID 442289644-Chloro-5-iodo-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Product 1

HCID 577138354-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-5-(5-(4-methylpiperazin-1-yl)pent-1-ynyl)-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-methyl-4-(pent-4-ynyl)piperazine, according to the general procedure A gave the title compound, as a solid. Mp=160.1-162.3° C. HPLC Rt=4.08 min.

Sources & evidence

ORD record
ord-907737c538024251bd9802085ad54757
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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