Diethyl Ether → Ethyl 2-cyclopropylpyrimidine-4-carbimidate

HRID 931084Notes

Reaction equation

HRID 931084 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(OCC)C.[Cl-].[NH4+]>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

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 2723922Sodium ethoxideHCID 898530762-Cyclopropylpyrimidine-4-carbonitrile

Product 1

HCID 89854162Ethyl 2-cyclopropylpyrimidine-4-carbimidate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-cyclopropylpyrimidine-4-carbonitrile (20.97 g, 144.5 mmol) in ethanol (100 mL) was added sodium ethoxide (1.8 g, 78.9 mmol of sodium metal in 30 mL of ethanol). The reaction mixture was stirred at room temperature for 30 minutes. Diethyl ether (300 mL) was added to the reaction mixture followed by a saturated aqueous solution of ammonium chloride (50 mL). The mixture was extracted with diethyl ether (100 mL×3). The combined organics were washed with brine (50 mL×2), dried over magnesium sulfate, filtered, concentrated under reduced pressure and dried under high vacuum to afford the title compound. The material was used without further purification. 1H NMR (500 MHz, CDCl3) δ 1.10-1.15 (m, 2H), 1.16-1.22 (m, 2H), 1.43 (t, 3H), 2.32 (tt, 1H), 4.44 (q, 2H), 7.50 (d, 1H), 8.72 (d, 1H).

Workup

  1. extractionThe mixture was extracted with diethyl ether (100 mL×3)
  2. washThe combined organics were washed with brine (50 mL×2)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-a327861f55a94afbaf6b69db173c9308
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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