Isopropanol → HCID 13374342, compound

HRID 223292Notes

Reaction equation

HRID 223292 reaction equation
[Na].[Cl:2][C:3]1[N:8]=[C:7](Cl)[C:6]([CH2:10][C:11]2[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[CH:5][N:4]=1.[CH:18]([OH:21])([CH3:20])[CH3:19]>>[Cl:2][C:3]1[N:8]=[C:7]([O:21][CH:18]([CH3:20])[CH3:19])[C:6]([CH2:10][C:11]2[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 3776Isopropanol2×HCID 5360545SodiumHCID 133743332,4-Dichloro-5-[(6-methyl-3-pyridinyl)methyl]pyrimidine

Product 1

HCID 13374342HCID 13374342, compoundYield 87%

Procedure

A solution of 1.38 g (0.06 g-atom) of sodium metal in 25 ml of isopropanol was heated to reflux until complete dissolution of the metal. The alkoxide solution was cooled to -10° and treated dropwise with a solution of 15.0 g (60 mmol) of 2,4-dichloro-5-[(6-methyl-3-pyridinyl)methyl]pyrimidine prepared as in Example 1 in 60 ml of isopropanol. The resulting mixture was allowed to warm to room temperature over 18 hours and was then concentrated. The resulting oil was dissolved in ethyl acetate, filtered, washed with water, dried over magnesium sulfate, filtered, concentrated and dried under vacuum to give 14.5 g (0.052 mol, 87%) of 2-chloro-4-isopropoxy-5-[(6-methyl-3-pyridinyl)methyl]pyrimidine. Recrystallization from ethyl acetate and petroleum ether gave yellow crystals: m.p. 38°-42°.

Workup

  1. temperatureto reflux until complete dissolution of the metal
  2. concentrationwas then concentrated
  3. dissolutionThe resulting oil was dissolved in ethyl acetate
  4. filtrationfiltered
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried under vacuum

Sources & evidence

ORD record
ord-25249ccef2084246b7c0500373fb895e
Source dataset
uspto-grants-1982_10
Patent number
US04352933

Reaction notes

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