Triethylamine → 4-Chloro-5-methoxy-6-(methoxymethyl)pyrimidine

HRID 1378400

Reaction equation

HRID 1378400 reaction equation
O[C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH2:10][O:11][CH3:12])[N:5]=[CH:4][N:3]=1.C(N(CC)CC)C.P(Cl)(Cl)([Cl:22])=O.C(=O)([O-])[O-].[Na+].[Na+]>ClC(Cl)C>[Cl:22][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH2:10][O:11][CH3:12])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178494688HCID 178494688, compound

Product 1

HCID 152793504-Chloro-5-methoxy-6-(methoxymethyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

85.0 g (0.5 mol) of 4-hydroxy-5-methoxy-6-methoxymethylpyrimidine were suspended in 600 ml of dichloroethane, 50.5 g of triethylamine were added, and 260 g (1.7 mol) of phosphorus oxychloride were then added without cooling. The mixture was stirred for 3 hours at 80° C., poured into ice-water and neutralized by adding solid sodium carbonate, the organic phase was separated, and the water phase was extracted several times by stirring with methylene chloride. The combined organic phases were dried and concentrated. The residue was distilled under a water pump vacuum. 66.1 g (70% of theory) of a yellow oil were obtained. B.p. 93°-96° C./0.1mm.

Workup

  1. temperaturewithout cooling
  2. customthe organic phase was separated
  3. extractionthe water phase was extracted several times
  4. stirringby stirring with methylene chloride
  5. customThe combined organic phases were dried
  6. concentrationconcentrated
  7. distillationThe residue was distilled under a water pump vacuum
  8. custom66.1 g (70% of theory) of a yellow oil were obtained

Sources & evidence

ORD record
ord-3d4eae15b48d410c83b87577a98525b3
Source dataset
uspto-grants-1997_09
Patent number
US05668140

Linked notes

Loading…