Phosphorus oxychloride → 4-Chloro-6-methyl-5-(propan-2-yl)pyrimidine

HRID 491272Notes

Reaction equation

HRID 491272 reaction equation
O[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([CH3:11])[N:5]=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:14])=O>CN(C=O)C>[Cl:14][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([CH3:11])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 178433210HCID 178433210, compound

Product 1

HCID 629159014-Chloro-6-methyl-5-(propan-2-yl)pyrimidineYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

4-Hydroxy-5-isopropyl-6-methylpyrimidine (12.2 g, 80 mmol) was added to 50 ml phosphorous oxychloride and treated with ca. 0.1 ml DMF. The mixture was heated to 60-70° C. and stirred for 2h. After cooling the excess POCl3 was removed under vacuum, the residue was poured onto ice and the pH of the aqueous layer was adjusted to 7 by addition of NaOH and NaHCO3. The product was taken up in dichloromethane, washed with sat. sodium bicarbonate, dried (Na2SO4) and evaporated. The residue was purified by vacuum distillation to yield 8.5 g (62 percent yield).

Workup

  1. customwas removed under vacuum
  2. additionthe residue was poured onto ice
  3. additionthe pH of the aqueous layer was adjusted to 7 by addition of NaOH and NaHCO3
  4. washwashed with sat. sodium bicarbonate
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. distillationThe residue was purified by vacuum distillation
  8. customto yield 8.5 g (62 percent yield)

Sources & evidence

ORD record
ord-eedf3db06ce14e51ac1739701e033ba5
Source dataset
uspto-grants-2009_05
Patent number
US07531482B2

Reaction notes

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