Sodium ethoxide → Ethyl 2-cyclopropylpyrimidine-4-carbimidate

HRID 931261Notes

Reaction equation

HRID 931261 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1.[O-:12][CH2:13][CH3:14].[Na+]>C(O)C>[CH:1]1([C:4]2[N:9]=[C:8]([C:10](=[NH:11])[O:12][CH2:13][CH3:14])[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 898530762-Cyclopropylpyrimidine-4-carbonitrile

Product 1

HCID 89854162Ethyl 2-cyclopropylpyrimidine-4-carbimidateYield 50.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-cyclopropylpyrimidine-4-carbonitrile (600 mg, 4.13 mmol) in ethanol (10 mL) was added sodium ethoxide (561.9 mg, 8.27 mmol). After 2 h, the mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford ethyl 2-cyclopropylpyrimidine-4-carbimidate (400 mg) as a pale yellow liquid. The material was used without further purification.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ffeb44eca3864f6c897e1cd143ad5351
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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