1-Butanol → 4-Chloro-N-ethylpyrimidin-2-amine

HRID 2120690Notes

Reaction equation

HRID 2120690 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.Cl.[CH2:10]([NH2:12])[CH3:11].C(N(CC)CC)C.C(O)CCC>CCCCCC.CCOC(C)=O.O>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:12][CH2:10][CH3:11])[N:7]=1

Participants

7

Reactant 4

HCID 2631-ButanolHCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 775312,4-Dichloropyrimidine

Product 1

HCID 234355174-Chloro-N-ethylpyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,4-dichloropyrimidine 21-1 (7.0 g, 47 mmol), ethylamine hydrochloride (5.75 g, 70.5 mmol), triethylamine (19.6 mL, 141 mmol) and n-butanol (150 mL) was heated at 90° C. for 6 hours. The solution was cooled, poured into water and extracted with EtOAc (2×). After washing with water then brine, the organic layer was dried (MgSO4) and concentrated to give an oil. Column chromatography (hexane:EtOAc 2:1 then 1:1) afforded the title compound 21-2 as the minor compound.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with EtOAc (2×)
  3. washAfter washing with water
  4. dry with materialbrine, the organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customto give an oil

Sources & evidence

ORD record
ord-aa0a0b337c754ba984c0633b98fb2bd8
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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