Sodium Carbonate → 5-(4-Amino-3-cyclohex-1-enyl-phenyl)-tetrahydro-pyrimidin-2-one

HRID 408911Notes

Reaction equation

HRID 408911 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][NH:18][C:17](=[O:20])[NH:16][CH2:15]2)=[CH:10][C:9]=1Br)(C)(C)C.[C:23]1(B(O)O)[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:15][NH:16][C:17](=[O:20])[NH:18][CH2:19]2)=[CH:10][C:9]=1[C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 38629021-Cyclohexenylboronic acidHCID 59771302[2-Bromo-4-(2-oxo-hexahydro-pyrimidin-5-yl)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 597712825-(4-Amino-3-cyclohex-1-enyl-phenyl)-tetrahydro-pyrimidin-2-one

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

[2-Bromo-4-(2-oxo-hexahydro-pyrimidin-5-yl)-phenyl]-carbamic acid tert-butyl ester (99 mg, 0.26 mmol, as prepared in the previous step) was dissolved in TFA (1 mL). The resulting mixture was stirred at RT for 30 min and concentrated in vacuo. The residue obtained was dried in vacuo for 1 h and dissolved in EtOH (0.5 mL) and toluene (1 mL). To this solution cyclohex-1-enyl boronic acid (20.5 mg, 0.16 mmol), 2M Na2CO3 (0.5 mL, 1 mmol) and Pd (PPh3)4 (30 mg, 0.025 mmol) were added. The resulting mixture was heated at 80° C. overnight. The reaction mixture was allowed to cool to RT and extracted with EtOAc (2×10 mL). The EtOAc layers were combined, dried (Na2SO4) and concentrated in vacuo. The residue obtained was purified on silica (2% MeOH-EtOAc) to afford the title compound (31 mg) contaminated with Ph3PO, which was used in the next step without further purification: Mass spectrum (ESI, m/z): Calcd. for C16H21N3O, 272.1 (M+H). found 272.1.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue obtained
  3. customwas dried in vacuo for 1 h
  4. dissolutiondissolved in EtOH (0.5 mL)
  5. temperatureThe resulting mixture was heated at 80° C. overnight
  6. temperatureto cool to RT
  7. extractionextracted with EtOAc (2×10 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue obtained
  11. customwas purified on silica (2% MeOH-EtOAc)

Sources & evidence

ORD record
ord-7fc3e042c54d4904b9722173ed138026
Source dataset
uspto-grants-2014_06
Patent number
US08759347B2

Reaction notes

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