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

HRID 1050993Notes

Reaction equation

HRID 1050993 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=O)C>[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 97%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

2-tert-butyl-6-cyclobutyl-pyrimdin-4-ol (3.15 g, 15.27 mmol) was dissolved in toluene (25 ml)/DMF (0.3 ml). POCl3 (3.5 mL, 38 mmol) was added dropwise at 10° C. The resulted solution was stirred at room temperature for 3 h then poured into water, extracted with DCM. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound (3.28 g, 97%). The crude material was used without further purification for the next step.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-823063c26c17473baf62688101a31702
Source dataset
uspto-grants-2016_07
Patent number
US09388148B2

Reaction notes

Loading…