Morpholine → HCID 86716006, compound

HRID 1482491Notes

Reaction equation

HRID 1482491 reaction equation
[N:1]1[CH:6]=[C:5]([CH:7]=O)[CH:4]=[N:3][CH:2]=1.[Si]([C:13]#[N:14])(C)(C)C.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.CC([O-])=O.[Na+].C([O-])([O-])=O.[Na+].[Na+]>CC(O)=O>[O:18]1[CH2:19][CH2:20][N:15]([CH:7]([C:5]2[CH:4]=[N:3][CH:2]=[N:1][CH:6]=2)[C:13]#[N:14])[CH2:16][CH2:17]1

Participants

7

Reactant 5

HCID 8083MorpholineHCID 10340Sodium CarbonateHCID 82115Trimethylsilyl cyanideHCID 517045Sodium AcetateHCID 2761034Pyrimidine-5-carboxaldehyde

Product 1

HCID 86716006HCID 86716006, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of pyrimidine-5-carbaldehyde (2 g, 18.52 mmol) and TMSCN (3.67 g, 37.0 mmol) in HOAc (50 mL) was added morpholine (2.42 g, 27.8 mmol) at room temperature and NaOAc (3.34 g, 40.7 mmol) was followed. The resulting mixture was stirred at room temperature overnight. Saturated aqueous Na2CO3 solution was added to quench the reaction mixture, the pH was adjusted to about 7 and extracted with EtOAc (3×100 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated to give crude 2-morpholino-2-(pyrimidin-5-yl)acetonitrile (2.5 g, yield: 66%). 1H NMR (CDCl3 400 MHz): δ9.25 (s, 1H), 8.92 (d, J=10.0 Hz, 2H), 4.87 (s, 1H), 3.79-3.70 (m, 4H), 2.67-2.56 (m, 4H).

Workup

  1. customto quench the reaction mixture
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6ce2b36b0bd04b66ab3158c24edbea84
Source dataset
uspto-grants-2016_08
Patent number
US09415055B2

Reaction notes

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