Potassium Carbonate → cis-2,6-Dimethyl-4-[4-(2-methyl-3-furanyl)-2-pyrimidinyl]morpholine

HRID 2278436Notes

Reaction equation

HRID 2278436 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:12]=[CH:11][O:10][C:9]=2[CH3:13])[CH:5]=[CH:4][N:3]=1.[CH3:14][C@H:15]1[O:20][C@@H:19]([CH3:21])[CH2:18][NH:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:21][C@H:19]1[O:20][C@@H:15]([CH3:14])[CH2:16][N:17]([C:2]2[N:7]=[C:6]([C:8]3[CH:12]=[CH:11][O:10][C:9]=3[CH3:13])[CH:5]=[CH:4][N:3]=2)[CH2:18]1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 6415002,6-Dimethylmorpholine, cis-2×HCID 867024262-Chloro-4-(2-methyl-3-furanyl)pyrimidine

Product 1

HCID 68056198cis-2,6-Dimethyl-4-[4-(2-methyl-3-furanyl)-2-pyrimidinyl]morpholineYield 76.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-4-(2-methyl-3-furanyl)pyrimidine (686 mg, 3.52 mmol), cis-2,6-dimethylmorpholine (447 mg, 3.88 mmol) and potassium carbonate (536 mg, 3.88 mmol) were added together in ethanol (16 mL) and the resulting mixture was heated under reflux for 4 hours. A further quantity of cis-2,6-dimethylmorpholine (122 mg, 1.057 mmol) and potassium carbonate (146 mg, 1.057 mmol) were added and the resulting mixture was heated under reflux for 4 hours. The reaction mixture was allowed to cool to room temperature and left to stand overnight. The reaction mixture was filtered, the filtrate evaporated under reduced pressure and the residue purified by SP4 Biotage column chromatography eluting with a gradient of 0-30% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound (737 mg, 2.70 mmol, 76% yield) as a colourless oil. LC/MS [M+H]+=274.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperaturethe resulting mixture was heated
  4. temperatureunder reflux for 4 hours
  5. waitleft
  6. filtrationThe reaction mixture was filtered
  7. customthe filtrate evaporated under reduced pressure
  8. customthe residue purified by SP4 Biotage column chromatography
  9. washeluting with a gradient of 0-30% ethyl acetate and iso-hexane
  10. additionProduct containing fractions
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6b7357a59dcd4bdcb91eeceb3f074637
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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