Methanol → 3-(4.6-Dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde dimethylacetal

HRID 653993Notes

Reaction equation

HRID 653993 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[C:13]([CH:18]=[O:19])=[N:14][CH:15]=[CH:16][CH:17]=2)[N:4]=1.[CH:20]([O-])([O-])[O:21]CC.[Cl-].[NH4+].[CH3:28]O>>[CH3:28][O:19][CH:18]([O:21][CH3:20])[C:13]1[C:12]([O:11][C:5]2[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[N:6]=2)=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 44155452-Pyridinecarboxaldehyde, 3-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-HCID 53630039Ethylorthoformate

Product 1

HCID 150028583-(4.6-Dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde dimethylacetalYield 90%

Procedure

A mixture consisting of 53.0 g of 3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-formylpyridine, 30.7 g of ethyl orthoformate, 0.48 g of ammonium chloride and 500 ml of methanol was heated under stirring at a reflux point for 5 hours. After the reaction mixture was cooled to room temperature, the precipitate was filtered off. The filtrate was concentrated under reduced pressure so that 56.1 g of 3-(4,6-dimethoxy-2-pyrimidinyloxy-2-pyridinecarboxaldehyde dimethylacetal were obtained (yield: 90%). A purified product was obtained by chromatography on a silica gel column.

Workup

  1. temperaturewas heated
  2. filtrationthe precipitate was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure so that 56.1 g of 3-(4,6-dimethoxy-2-pyrimidinyloxy-2-pyridinecarboxaldehyde dimethylacetal
  4. customwere obtained (yield: 90%)
  5. customA purified product was obtained by chromatography on a silica gel column

Sources & evidence

ORD record
ord-80e8dcfce3aa4d52a18755485f48848b
Source dataset
uspto-grants-1992_07
Patent number
US05129937

Reaction notes

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