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

HRID 388090Notes

Reaction equation

HRID 388090 reaction equation
[NH2:1][C:2]1[C:3]([NH:18][C@H:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][OH:21])=[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.NC1C(N[C@H](C2C=CC=CC=2)[CH2:38][OH:39])=NC(Br)=CN=1.N1C2C=CC=C(B(O)O)C=2C=CC=1.C(=O)([O-])[O-].[K+].[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=O.O>[OH:21][CH2:20][C@H:19]([N:18]1[C:3]2=[N:4][C:5]([C:8]3[CH:17]=[CH:16][CH:15]=[C:14]4[C:9]=3[CH:10]=[CH:11][CH:12]=[N:13]4)=[CH:6][N:7]=[C:2]2[NH:1][C:38]1=[O:39])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 5153389Quinolin-5-ylboronic acidHCID 66699883(R)-2-(3-Amino-6-(quinolin-5-yl)pyrazin-2-ylamino)-2-phenylethanolHCID 86626383(R)-2-(3-Amino-6-bromopyrazin-2-ylamino)-2-phenylethanol

Product 1

HCID 66699661(R)-1-(2-Hydroxy-1-phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-oneYield 67%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(R)-2-(3-Amino-6-(quinolin-5-yl)pyrazin-2-ylamino)-2-phenylethanol. (R)-2-(3-Amino-6-bromopyrazin-2-ylamino)-2-phenylethanol (0.700 g, 2.26 mmol), quinoline-5-boronic acid (0.431 g, 2.48 mmol), tetrakis(triphenylphosphine)-palladium (0.287 g, 0.226 mmol), potassium carbonate (1.24 g, 9.04 mmol), water (8 mL) and dimethylformamide (35 mL) were reacted according to General Procedure B. The crude material was purified via Biotage silica gel chromatography (40-100% ethyl acetate/hexanes, 40S column) to afford the title compound (0.546 g, 67% yield). MS (ESI) m/z 358.3 [M+1]+.

Workup

  1. customThe crude material was purified via Biotage silica gel chromatography (40-100% ethyl acetate/hexanes, 40S column)

Sources & evidence

ORD record
ord-6b82a80abef44d32a1dbd67b80dfdd53
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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