2-Methoxyethanol → HCID 13374344, compound

HRID 1632799Notes

Reaction equation

HRID 1632799 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[CH:4][N:3]=1.[Na].[CH3:18][O:19][CH2:20][CH2:21][OH:22]>>[Cl:1][C:2]1[N:7]=[C:6]([O:22][CH2:21][CH2:20][O:19][CH3:18])[C:5]([CH2:9][C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 80192-Methoxyethanol2×HCID 5360545SodiumHCID 133743332,4-Dichloro-5-[(6-methyl-3-pyridinyl)methyl]pyrimidine

Product 1

HCID 13374344HCID 13374344, compoundYield 78%

Procedure

To a stirred solution of 44.6 g (0.176 mol) of 2,4-dichloro-5-[(6-methyl-3-pyridinyl)methyl]pyrimidine from Example 1 in 300 ml of 2-methoxyethanol at 0°-5° was added dropwise over 2 hours a solution of 4.25 g (0.177 g-atom) of sodium metal in 250 ml of 2-methoxyethanol. The solution was stirred for 30 minutes at 5°, concentrated and the resulting oil dissolved in 500 ml of ethyl acetate. The solution was washed with water, dried over sodium sulfate, filtered and concentrated to give 40.4 g (0.137 mol, 78%) of 2-chloro-4-(2-methoxyethoxy)-5-[(6-methyl-3-pyridinyl)methyl]pyrimidine: m.p. 50°-52°.

Workup

  1. concentrationconcentrated
  2. dissolutionthe resulting oil dissolved in 500 ml of ethyl acetate
  3. washThe solution was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4e47062378844f0499f48b405033b25d
Source dataset
uspto-grants-1984_10
Patent number
US04477663

Reaction notes

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