N-Methyl dicyclohexylamine → HCID 86723420, compound

HRID 2201176Notes

Reaction equation

HRID 2201176 reaction equation
[CH3:1][N:2]1[C:7]2=[C:8]3[N:13]([C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:6]2[C:5](=[O:21])[N:4]([CH3:22])[C:3]1=[O:23])[CH2:12][CH2:11][CH:10]=[CH:9]3.Br[C:25]1[O:26][C:27]([CH3:30])=[CH:28][CH:29]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C1(N(C2CCCCC2)C)CCCCC1>CC(N(C)C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][N:2]1[C:7]2=[C:8]3[N:13]([C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:6]2[C:5](=[O:21])[N:4]([CH3:22])[C:3]1=[O:23])[CH2:12][CH2:11][CH:10]=[C:9]3[C:25]1[O:26][C:27]([CH3:30])=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 24210N-Methyl dicyclohexylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 6384482-bromo-5-methylfuranHCID 86723419HCID 86723419, compound2×

Product 1

HCID 86723420HCID 86723420, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

1,3-dimethyl-5-phenyl-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione (Intermediate I), 2-bromo-5-methylfuran (commercially available) (390 mg, 2.421 mmol), palladium acetate (commercially available) (36.2 mg, 0.161 mmol), tri-tert-butylphosphine tetrafluorohydroborate (commercially available) (94 mg, 0.323 mmol) and N-cyclohexyl-N-methylcyclohexylamine (commercially available) (0.691 mL, 3.23 mmol) were combined in dimethyl acetamide (4 mL) and the mixture sparged with nitrogen for 30 min. The mixture was then heated at 120° C. for 15 h under microwave irradiation. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic phases were washed with brine, dried over sodium sulphate and evaporated under reduced pressure. Purification by chromatography on silica, eluting with 20% EtOAc in iso-hexane, afforded 1,3-dimethyl-10-(5-methylfuran-2-yl)-5-phenyl-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione as a yellow solid which was used without further purification.

Workup

  1. customthe mixture sparged with nitrogen for 30 min
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customPurification by chromatography on silica
  8. washeluting with 20% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-370ba8d0a8b243fb9264a91afebe289b
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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