Morpholine → HCID 68364832, compound

HRID 1482484Notes

Reaction equation

HRID 1482484 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[CH:5][N:4]=1.[Si]([C:17]#[N:18])(C)(C)C.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.CC([O-])=O.[Na+]>CC(O)=O>[N:19]1([CH:9]([C:6]2[CH:5]=[N:4][C:3]([C:2]([F:12])([F:11])[F:1])=[N:8][CH:7]=2)[C:17]#[N:18])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 82115Trimethylsilyl cyanideHCID 517045Sodium AcetateHCID 177509412-(Trifluoromethyl)pyrimidine-5-carbaldehyde

Product 1

HCID 68364832HCID 68364832, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 2-trifluoromethyl-pyrimidine-5-carbaldehyde (572 mg, 3.25 mmol) and TMSCN (645 mg, 6.49 mmol) in HOAc (10 ml) was added dropwise morpholine (311 mg, 3.57 mmol), followed by NaOAc (320 mg, 3.90 mmol). The mixture was stirred at room temperature overnight. The solvent was removed in vacuum. The residue was basified by addition of sat. aq. NaHCO3 solution to pH 8; then extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to yield the title compound (591 mg, yield: 67%). 1H NMR (CDCl3 400 MHz): δ ppm 9.10 (s, 2H), 4.96 (s, 1H), 3.88-3.71 (m, 4H), 2.79-2.55 (m, 4H).

Workup

  1. customThe solvent was removed in vacuum
  2. additionThe residue was basified by addition of sat. aq. NaHCO3 solution to pH 8
  3. extractionthen extracted with EtOAc (3×10 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a4365c6c0a804bb3a5c85f9717991e35
Source dataset
uspto-grants-2016_08
Patent number
US09415055B2

Reaction notes

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