Ethyl 2,4,6-trimethylpyrimidine-5-carboxylate → HCID 13934576, compound

HRID 542663Notes

Reaction equation

HRID 542663 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9](OCC)=[O:10])=[C:4]([CH3:14])[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:10][CH2:9][C:5]1[C:6]([CH3:8])=[N:7][C:2]([CH3:1])=[N:3][C:4]=1[CH3:14]

Participants

4

Reactant 2

HCID 13203796Ethyl 2,4,6-trimethylpyrimidine-5-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 13934576HCID 13934576, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(a) Ethyl 2,4,6-trimethylpyrimidine-5-carboxylate [11.0 g; prepared according to Urban & Shnider, Helv. Chim Acta, 41, 1806 (1958)] was stirred with a slight excess of lithium aluminium hydride in dry tetrahydrofuran (100 ml) at room temperature for 2 hr. The solvent was evaporated and the residue was shaken with a little water. The dried (MgSO4) ethyl acetate extract was evaporated and the residue was purified by column chromotography over alumina with ethyl acetate elution to give 5-(hydroxymethyl)-2,4,6-trimethylpyrimidine as white crystals, mp 68° C.

Workup

  1. customThe solvent was evaporated
  2. dry with materialThe dried (MgSO4) ethyl acetate
  3. extractionextract
  4. customwas evaporated
  5. customthe residue was purified by column chromotography over alumina with ethyl acetate elution

Sources & evidence

ORD record
ord-60112536e4e041d688689ee815bf6656
Source dataset
uspto-grants-1987_04
Patent number
US04659362

Reaction notes

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