Dimethylformamide → HCID 58446856, compound

HRID 1958344Notes

Reaction equation

HRID 1958344 reaction equation
Br.[NH2:2][C:3]1[N:8]=[CH:7][N:6]2[CH:9]=[C:10]([C:12]3[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=3)[N:11]=[C:5]2[CH:4]=1.CN(C=O)C.[CH3:24][O:25][C:26](=[O:29])[CH2:27]Br.C([O-])([O-])=O.[Cs+].[Cs+]>C(Cl)Cl.CO>[CH3:24][O:25][C:26](=[O:29])[CH2:27][O:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:10]2[N:11]=[C:7]3[N:8]=[C:3]([NH2:2])[CH:4]=[CH:5][N:6]3[CH:9]=2)[CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 67391653HCID 67391653, compound

Product 1

HCID 58446856HCID 58446856, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
65 °C

Procedure

3-(7-Aminoimidazo[1,2-c]pyrimidin-2-yl)phenol hydrobromide (100 mg, 0.33 mmol) was combined with DMF (0.2 ml) to give a light brown suspension. Methyl-2-bromoacetate (55 mg, 0.36 mmol) and Cs2CO3 (424 mg, 1.3 mmol) were added, and the reaction mixture was stirred 2 h in a sealed tube at 65° C. The reaction mixture was directly put on a column and the product was isolated by flash chromatography (SiO2—NH2 cartridge; eluent: CH2Cl2/MeOH 95:05) to yield the title compound (57 mg, 58%) as a light yellow solid. MS (m/z)=299.1 [M+H+].

Workup

  1. customto give a light brown suspension

Sources & evidence

ORD record
ord-3a653cb06176483d961131fb6f5ef93a
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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