Sodium Bicarbonate → 2-Cyclobutylpyrimidine-4-carbaldehyde

HRID 931111Notes

Reaction equation

HRID 931111 reaction equation
[CH:1]1([C:5]2[N:10]=[C:9]([CH:11](OC)[O:12]C)[CH:8]=[CH:7][N:6]=2)[CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+]>Cl.O>[CH:1]1([C:5]2[N:10]=[C:9]([CH:11]=[O:12])[CH:8]=[CH:7][N:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 898540422-Cyclobutyl-4-(dimethoxymethyl)pyrimidine

Product 1

HCID 649856792-Cyclobutylpyrimidine-4-carbaldehydeYield 88.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2-cyclobutyl-4-(dimethoxymethyl)pyrimidine (300 mg, 1.4 mmol) in aqueous hydrochloric acid (3N, 5 mL) was heated to 50° C. for 16 h. The reaction mixture was cooled to room temperature, then was diluted with water, neutralized with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The combined organics were dried over sodium sulfate and concentrated under reduced pressure to afford the title compound as a brown colored liquid (200 mg). MS (ES+) (M+H) 163.16.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bfecea20e2114472a57de09725ef0c8a
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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