Phosphorus oxychloride → 2-tert-Butyl-4-chloro-6-cyclopropyl-pyrimidine

HRID 219694Notes

Reaction equation

HRID 219694 reaction equation
[C:1]([C:5]1[N:10]=[C:9](O)[CH:8]=[C:7]([CH:12]2[CH2:14][CH2:13]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O=P(Cl)(Cl)[Cl:17]>C1(C)C=CC=CC=1.CN(C)C=O>[C:1]([C:5]1[N:10]=[C:9]([Cl:17])[CH:8]=[C:7]([CH:12]2[CH2:14][CH2:13]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178441865HCID 178441865, compound

Product 1

HCID 633553042-tert-Butyl-4-chloro-6-cyclopropyl-pyrimidineYield 104.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

14.8 g 2-tert-butyl-4-hydroxy-6-cyclopropyl-pyrimidine (76.9 mmol) were dissolved in 100 ml of toluene and 3 ml of dimethylformamide. 23.6 ml of POCl3 (153.7 mmol) were added dropwise at 10° C. After stirring overnight at room temperature most of the toluene was evaporated. The mixture was cooled with ice and 20 ml of water were added cautiously. Subsequently, an additional 200 ml of water were added and the aqueous phase was extracted four times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered, and then concentrated to dryness to yield 17 g of a yellowish oil (quant.).

Workup

  1. customwas evaporated
  2. temperatureThe mixture was cooled with ice and 20 ml of water
  3. additionwere added cautiously
  4. additionSubsequently, an additional 200 ml of water were added
  5. extractionthe aqueous phase was extracted four times with dichloromethane
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8f760cff3ce9466ea5589371ac324223
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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