Phosphorus oxychloride → 4-[4-Chloro-5-(2-chloro-5-methoxy-phenoxy)-6-methyl-pyrimidin-2-yl]-morpholine

HRID 37092Notes

Reaction equation

HRID 37092 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:3]=1[O:4][C:5]1[C:6](O)=[N:7][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:9][C:10]=1[CH3:11].O=P(Cl)(Cl)[Cl:27]>>[Cl:27][C:6]1[C:5]([O:4][C:3]2[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:2]=2[Cl:1])=[C:10]([CH3:11])[N:9]=[C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178490743HCID 178490743, compound

Product 1

HCID 189389104-[4-Chloro-5-(2-chloro-5-methoxy-phenoxy)-6-methyl-pyrimidin-2-yl]-morpholine

Conditions

Temperature
120 °C

Procedure

1.72 g of 5-(2-chloro-5-methoxy-phenoxy)-6-methyl-2-(morpholin-4-yl)-pyrimidin-4-ol were mixed with 3.3 ml of POCl3. The reaction mixture was stirred at 120° C. for 2 hours, thereafter the excess reagent was distilled off. The residue was taken up in chloroform and washed with water, 1N NaOH and water. The organic phase was dried, concentrated and the residue was recrystallized from ether. There were obtained 1.48 g of 4-[4-chloro-5-(2-chloro-5-methoxy-phenoxy)-6-methyl-pyrimidin-2-yl]-morpholine, m.p. 134° C., MS: M=369.

Workup

  1. distillationthe excess reagent was distilled off
  2. washwashed with water, 1N NaOH and water
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-3b33783162bb4d9c83d67abdefe98317
Source dataset
uspto-grants-1995_05
Patent number
US05420129

Reaction notes

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