Reaction #632042

Reaction equation

2-[2-(pyridin-2-yl)-ethoxy]-4-(methoxycarbonyl)-6-(morpholin-4-yl)-pyrimidine

ethanol sodium borohydride

→

2-[2-(pyridin-2-yl)-ethoxy]-4-formyl-6-(morpholin-4-yl)-pyrimidine

Yield 48.0%

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturethe reaction mixture was refluxed for 3 hours
2. 2
   OtherSolvent was removed
3. 3
   Washwashed with brine
4. 4
   Otherdried
5. 5
   Concentrationconcentrated
6. 6
   Otherto give crude alcohol

Procedure

Preparation of alcohol derivative used to prepare Compounds 1-4: To a solution of 2-[2-(pyridin-2-yl)-ethoxy]-4-(methoxycarbonyl)-6-(morpholin-4-yl)-pyrimidine (0.81 g, 2.35 mmol) in ethanol sodium borohydride (4 eq, 0.36 g) was added in portions and the reaction mixture was refluxed for 3 hours. Solvent was removed, the reaction mixture distributed between ethyl acetate and water, organic solution washed with brine, dried and concentrated to give crude alcohol. The above alcohol (0.64 g, 2 mmol) was heated in toluene at 85° C. with manganese dioxide, (10 eq, 1.75 g) for 4 hours to give 2-[2-(pyridin-2-yl)-ethoxy]-4-formyl-6-(morpholin-4-yl)-pyrimidine (0.3 g, 48%) which was isolated by column chromatography.

Source