Ethanol → HCID 20195958, compound

HRID 223290Notes

Reaction equation

HRID 223290 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].[CH2:18]([OH:20])[CH3:19]>>[Cl:1][C:2]1[N:7]=[C:6]([O:20][CH2:18][CH3:19])[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 702Ethanol2×HCID 5360545SodiumHCID 133743332,4-Dichloro-5-[(6-methyl-3-pyridinyl)methyl]pyrimidine

Product 1

HCID 20195958HCID 20195958, compoundYield 90%

Procedure

To a stirred solution of 8.1 g (32 mmol) of 2,4-dichloro-5-[(6-methyl-3-pyridinyl)methyl]pyrimidine prepared as in Example 1 in 200 ml of ethanol at 10° was added dropwise over 1 hour a solution of 0.8 g (35 mg-atom) of sodium metal in 100 ml of ethanol. The resulting mixture was stirred for 18 hours at room temperature, concentrated, and the resulting oil dissolved in 100 ml of ethyl acetate. The resulting solution was washed with water, dried over sodium sulfate, filtered and concentrated to give 7.6 g (0.0288 mmol, 90%) of 2-chloro-4-ethoxy-5-[(6-methyl-3-pyridinyl)methyl]pyrimidine; MS(FD)m/e 263 parent ion.

Workup

  1. concentrationconcentrated
  2. dissolutionthe resulting oil dissolved in 100 ml of ethyl acetate
  3. washThe resulting solution was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bdfb4f4497264a78bacc1fab869a62bd
Source dataset
uspto-grants-1982_10
Patent number
US04352933

Reaction notes

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