Ethylamine → (5-Bromo-4-methoxy-pyrimidin-2-yl)-ethyl-amine

HRID 445774Notes

Reaction equation

HRID 445774 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH2:11]([NH2:13])[CH3:12]>C1COCC1.CO.CCOC(C)=O>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5]([NH:13][CH2:11][CH3:12])=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 6341EthylamineHCID 36631435-Bromo-2-chloro-4-methoxypyrimidine

Product 1

HCID 59613034(5-Bromo-4-methoxy-pyrimidin-2-yl)-ethyl-amine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-bromo-2-chloro-4-methoxypyrimidine (Frontier Scientific, Logan, USA, 0.895 mmol) in THF (2.5 ml) cooled with an ice-bath was added a 2 M solution of ethylamine in MeOH (Aldrich, Buchs, Switzerland, 0.492 ml). The RM was stirred at 0° C. for 1 h and at rt for 66 h then the reaction mixture was diluted with EtOAc, washed with saturated aqueous NaHCO3, with brine, dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and purified by flash chromatography (CH2Cl2/iPrOH 0% to 6%) to give after evaporation of the fractions containing the title compound an off-white solid. (HPLC: tR 2.16min (Method A); M+H=232, 234 MS-ES)

Workup

  1. washwashed with saturated aqueous NaHCO3, with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was absorbed on silica gel
  6. custompurified by flash chromatography (CH2Cl2/iPrOH 0% to 6%)
  7. customto give
  8. customafter evaporation of the fractions
  9. additioncontaining the title compound an off-white solid

Sources & evidence

ORD record
ord-5558d6335e714838ad4ddd05f6eb6b58
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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