Water → 2-Tert-butyl-4-chloro-6-cyclobutyl-pyrimidine

HRID 219690Notes

Reaction equation

HRID 219690 reaction equation
[C:1]([C:5]1[N:10]=[C:9](O)[CH:8]=[C:7]([CH:12]2[CH2:15][CH2:14][CH2:13]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O=P(Cl)(Cl)[Cl:18].O>C1(C)C=CC=CC=1.CN(C)C=O>[C:1]([C:5]1[N:10]=[C:9]([Cl:18])[CH:8]=[C:7]([CH:12]2[CH2:15][CH2:14][CH2:13]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 178441866HCID 178441866, compound

Product 1

HCID 860953852-Tert-butyl-4-chloro-6-cyclobutyl-pyrimidineYield 100.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

9.9 g of 2-tert-butyl-4-hydroxy-6-cyclobutyl-pyrimidine (48 mmol) were dissolved in 80 ml of toluene and 1 ml of dimethylformamide. 10.7 ml of POCl3 (114.8 mmol) were added dropwise at 10° C. Stirring was continued for 3 h at room temperature. The reaction mixture was poured into water, and the aqueous layer extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and then concentrated to dryness to give 10.8 g of a yellowish oil (quant.).

Workup

  1. extractionthe aqueous layer extracted with dichloromethane
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3d8b2244c02d4e759dc2fc308cd48748
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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