Methyl iodide → 1-(7-Amino-5-(1-methylpiperidin-4-yl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone

HRID 2047135Notes

Reaction equation

HRID 2047135 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:15][CH:16]=3)=[C:6]2[N:5]=[C:4]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:3]=1[C:29](=[O:31])[CH3:30].[CH3:32]I>CN(C=O)C>[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:15][CH:16]=3)=[C:6]2[N:5]=[C:4]([CH:23]2[CH2:24][CH2:25][N:26]([CH3:32])[CH2:27][CH2:28]2)[C:3]=1[C:29](=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 667379881-(7-Amino-3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone

Product 1

HCID 674943491-(7-Amino-5-(1-methylpiperidin-4-yl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(7-amino-3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone (25 mg, 0.06 mmol), DEA (52 μL, 0.3 mmol) in DMF (1 mL) was added MeI (15 μL, 0.24 mmol). The reaction mixture was stirred for one hour and directly purified by HPLC to provide the title compound. LC/MS RT=2.76 min. Mass calculated for M+H 427.2, observed 427.3.

Workup

  1. customdirectly purified by HPLC

Sources & evidence

ORD record
ord-989fa0d336da45da8f2d9beffe826ca5
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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