Potassium Carbonate → 1-(4-Methoxybenzyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

HRID 1014679Notes

Reaction equation

HRID 1014679 reaction equation
[NH2:1][C:2]1[C:3]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[N:4][C:5]([C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[N:13]3)=[CH:6][N:7]=1.BrC1N=C(NCC2C=C[C:40]([O:43]C)=CC=2)C(N)=NC=1.N1C2C=CC=C(B(O)O)C=2C=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C=O.O>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:18]2[C:3]3=[N:4][C:5]([C:8]4[CH:17]=[CH:16][CH:15]=[C:14]5[C:9]=4[CH:10]=[CH:11][CH:12]=[N:13]5)=[CH:6][N:7]=[C:2]3[NH:1][C:40]2=[O:43])=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 5153389Quinolin-5-ylboronic acidHCID 248204296-Bromo-N2-(4-methoxybenzyl)pyrazine-2,3-diamineHCID 66699817(3-Amino-6-(5-quinolyl)pyrazin-2-yl)[(4-methoxyphenyl)methyl]amine

Product 1

HCID 666996241-(4-Methoxybenzyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-oneYield 15%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(3-Amino-6-(5-quinolyl)pyrazin-2-yl)[(4-methoxyphenyl)methyl]amine. 6-Bromo-N2-(4-methoxybenzyl)pyrazine-2,3-diamine (0.928 g, 3.00 mmol), quinoline-5-boronic acid (0.675 g, 3.9 mmol), tetrakis(triphenylphosphine)palladium (0.306 g, 0.265 mmol), potassium carbonate (1.10 g, 7.95 mmol), water (7 ml) and dimethylformamide (35 mL) were reacted according to General Procedure B. The crude material was purified via Biotage silica gel chromatography (0-10% methanol in dichloromethane) followed by triturating with water/methanol to afford the title compound (0.165 g, 15% yield). MS (ESI) m/z 358.3 [M+1]+.

Workup

  1. customThe crude material was purified via Biotage silica gel chromatography (0-10% methanol in dichloromethane)
  2. customby triturating with water/methanol

Sources & evidence

ORD record
ord-b4b3c13490274034ba8f91005856d9b6
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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