HCID 53251307, compound → HCID 69932368, compound

HRID 509622Notes

Reaction equation

HRID 509622 reaction equation
[CH3:1][C:2]1[N:7]2[CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]3[N:14]([CH3:23])[CH:15]=[C:16]([C:18]4[S:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)[N:10]=[C:6]2[N:5]=[C:4]([CH3:24])[CH:3]=1.[H][H]>CO.[Pd]>[CH3:1][C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][CH2:12][C:13]3[N:14]([CH3:23])[CH:15]=[C:16]([C:18]4[S:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)[N:10]=[C:6]2[N:5]=[C:4]([CH3:24])[CH:3]=1

Participants

5

Reactant 2

HCID 53251307HCID 53251307, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69932368HCID 69932368, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5,7-Dimethyl-2-[(E)-2-(1-methyl-4-thiophen-2-yl-1H-imidazol-2-yl)-vinyl]imidazo[1,2-a]pyrimidine (40 mg, 0.083 mmol) in methanol (2 mL) was passed through a H-Cube® Continuous-flow Hydrogenation Reactor (ThalesNano) at a flow rate of 1 mL/min through a small cartridge of 10% Pd/C (THS01111) with an internal temperature of 40° C. and 30 bar of hydrogen pressure. Evaporation of the volatiles afforded the title compound (11.6 mg, 41%). LC-MS: m/z=338.6 (MH+), tR=0.69 minutes, method A.

Workup

  1. customEvaporation of the volatiles

Sources & evidence

ORD record
ord-4fb52a59263949b0b0709ba5d66c8e68
Source dataset
uspto-grants-2015_08
Patent number
US09096589B2

Reaction notes

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