Cesium carbonate → 2-Chloro-4-(3-methoxypropoxy)pyrimidine

HRID 410399Notes

Reaction equation

HRID 410399 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH3:9][O:10][CH2:11][CH2:12][CH2:13][OH:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cl-].[Na+].O>[Cl:1][C:2]1[N:7]=[C:6]([O:14][CH2:13][CH2:12][CH2:11][O:10][CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 741163-Methoxy-1-propanolHCID 775312,4-Dichloropyrimidine

Product 1

HCID 623358332-Chloro-4-(3-methoxypropoxy)pyrimidineYield 33%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

2,4-Dichloropyrimidine (250 mg, 1.678 mmol), 3-methoxy-1-propanol (0.193 ml, 2.014 mmol), and cesium carbonate (929 mg, 2.85 mmol) were combined in DMF (5 ml). The suspension was heated to 80° C. for 15 h. The mixture was allowed to cool to room temperature, diluted with brine and extracted with EtOAc (3×). The organic layer was dried over Na2SO4 and concentrated in vacuo. Purification via flash chromatography (5-15% EtOAc:Hexanes) gave 2-chloro-4-(3-methoxypropoxy)pyrimidine (112 mg, 33%) as a colorless oil. MS ESI: [M+H]+ m/z 203.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification via flash chromatography (5-15% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-c2789536587741bb83f167c009fd4526
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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