Ethylamine → 4-Chloro-6-(ethylamino)pyrimidine

HRID 1038711Notes

Reaction equation

HRID 1038711 reaction equation
[CH2:1]([NH2:3])[CH3:2].Cl[C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[CH:7][N:6]=1>CCO>[Cl:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]([NH:3][CH2:1][CH3:2])[CH:10]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 709434,6-Dichloropyrimidine

Product 1

HCID 5884524-Chloro-6-(ethylamino)pyrimidineYield 174.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethylamine (70% in water, 16 ml, 45.08 mmol, 2.5 eq.) is added dropwise (15 min) to a suspension of 4,6-dichloropyrimidine (12 g, 80.5 mmol) in EtOH (36 ml) at RT. The resulting yellowish solution is allowed to stir for 1 h at RT and then cooled to 0° C. The resulting white precipitate is collected by vacuum filtration, washed with water and dried in vacuo to afford 12.4 g of the title compound: ESI-MS: 157.9 [MH]+; single peak at tR=2.02 min (purity: 100%, gradient J).

Workup

  1. temperaturecooled to 0° C
  2. filtrationThe resulting white precipitate is collected by vacuum filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7752d830b7024f79b0e3b4acfb6adb48
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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