Isopropylamine → 1-(2-Chloro-4-isopropylaminopyrimidin-5-yl)-ethanone

HRID 475322Notes

Reaction equation

HRID 475322 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9](=[O:11])[CH3:10])=[CH:4][N:3]=1.C(=O)([O-])O.[Na+].[CH:17]([NH2:20])([CH3:19])[CH3:18].C1CCCCC1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:20][CH:17]([CH3:19])[CH3:18])[C:5]([C:9](=[O:11])[CH3:10])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 8078CyclohexaneHCID 516892Sodium BicarbonateHCID 212747081-(2,4-Dichloropyrimidin-5-yl)ethan-1-one

Product 1

HCID 574611371-(2-Chloro-4-isopropylaminopyrimidin-5-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2,4-dichloro-pyrimidin-5-yl)-ethanone (10 g, 0.052 mol), sodium hydrogen carbonate (19.35 g, 0.058 mol) and isopropylamine (5 mL, 0.058 mol) are taken up in 35 mL THF and 200 mL cyclohexane and stirred for 2 h at 20° C. The reaction solution is filtered through silica gel, the solvent is eliminated in vacuo and 1-(2-chloro-4-isopropylaminopyrimidin-5-yl)-ethanone (HPLC-MS: tRet.=1.73 min, MS(M+H)+=214/216; method FECB3) is obtained.

Workup

  1. filtrationThe reaction solution is filtered through silica gel

Sources & evidence

ORD record
ord-68033b788dce4a37b212e189f222e7ac
Source dataset
uspto-grants-2014_01
Patent number
US08637549B2

Reaction notes

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