Morpholine → HCID 66970300, compound

HRID 1365898Notes

Reaction equation

HRID 1365898 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][C:17]2[CH:18]=[C:19]([C:23]3[N:28]=[C:27]([C:29]4[C:30]([O:37][CH3:38])=[N:31][C:32]([O:35][CH3:36])=[N:33][CH:34]=4)[CH:26]=[C:25](Cl)[N:24]=3)[CH:20]=[CH:21][CH:22]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>C(#N)C>[CH3:36][O:35][C:32]1[N:31]=[C:30]([O:37][CH3:38])[C:29]([C:27]2[CH:26]=[C:25]([N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[N:24]=[C:23]([C:19]3[CH:20]=[CH:21][CH:22]=[C:17]([NH:16][C:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[O:15])[CH:18]=3)[N:28]=2)=[CH:34][N:33]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86630890HCID 86630890, compound

Product 1

HCID 66970300HCID 66970300, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-[3-(1-tert-butoxycarbonylpiperidin-4-ylcarbonylamino)phenyl]-6-chloro-4-(2,4-dimethoxypyrimidin-5-yl)pyrimidine (0.072 g), morpholine (0.056 g) and acetonitrile (2.5 ml) was stirred under an atmosphere of nitrogen and heated to 100° C. for 5 minutes using microwave radiation. The reaction mixture was evaporated. Toluene was added and the mixture was re-evaporated. Trifluoroacetic acid (3 ml) was added to the material so obtained and the mixture was stirred at ambient temperature for 3 hours. The mixture was evaporated. Toluene was added and the mixture was re-evaporated and the residue was purified by column chromatography on an ‘Isolute SCX’ column (1 g) by initially washing the column with methylene chloride and then with methanol (5 ml) followed by elution with a 7M methanolic ammonia solution. The material so obtained was dried under vacuum. There was thus obtained the title compound as a solid (0.019 g); NMR Spectrum: (CDCl3) 1.68-1.84 (m, 2H), 1.91-2.0 (m, 2H), 2.37-2.5 (m, 1H), 2.63-2.76 (m, 2H), 3.14-3.27 (m, 2H), 3.74-3.91 (m, 8H), 7.07 (s, 1H), 7.12 (s, 1H), 7.42 (t, 1H), 8.03 (d, 1H), 8.21 (d, 1H), 8.31 (s, 1H), 9.37 (s, 1H); Mass Spectrum: M+H+ 506.

Workup

  1. customThe reaction mixture was evaporated
  2. additionToluene was added
  3. customthe mixture was re-evaporated
  4. additionTrifluoroacetic acid (3 ml) was added to the material
  5. customso obtained
  6. stirringthe mixture was stirred at ambient temperature for 3 hours
  7. customThe mixture was evaporated
  8. additionToluene was added
  9. customthe mixture was re-evaporated
  10. customthe residue was purified by column chromatography on an ‘Isolute SCX’ column (1 g)
  11. washby initially washing the column with methylene chloride
  12. washwith methanol (5 ml) followed by elution with a 7M methanolic ammonia solution
  13. customThe material so obtained
  14. customwas dried under vacuum

Sources & evidence

ORD record
ord-f67d8adab52c4eaaa99d84ff40607bbf
Source dataset
uspto-grants-2011_02
Patent number
US07893063B2

Reaction notes

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