Triethylamine → HCID 86723527, compound

HRID 2201294Notes

Reaction equation

HRID 2201294 reaction equation
[C:1]([C:9]1[C:10](=[O:22])[N:11]([CH2:20][CH3:21])[C:12](=[O:19])[N:13]([CH2:17][CH3:18])[C:14]=1[CH2:15]Br)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([S:42][CH2:43][CH2:44][NH2:45])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>CCO>[CH2:17]([N:13]1[C:14]2=[CH:15][N:45]([CH2:44][CH2:43][S:42][C:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:9]2[C:10](=[O:22])[N:11]([CH2:20][CH3:21])[C:12]1=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 262764S-TritylcysteamineHCID 86723528HCID 86723528, compound

Product 1

HCID 86723527HCID 86723527, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Benzoyl-6-(bromomethyl)-1,3-diethylpyrimidine-2,4(1H,3H)-dione (step 3) (850 mg, 2.327 mmol), 2-(tritylthio)ethanamine (commercially available, 1115 mg, 3.49 mmol) and triethylamine (0.973 mL, 6.98 mmol) were combined in EtOH (Volume: 20 mL) and the mixture heated at reflux for 20 mins. The reaction mixture was cooled to RT and evaporated under vacuum. The residue was partitioned between DCM and water and extracted with DCM. The organic phase was passed through a hydrophobic frit and evaporated onto silica. The silica was deposited onto a 10 g silica cartridge and purification by chromatography on silica eluting with 10-50% EtOAc in iso-hexane afforded the title compound as a white solid;

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 20 mins
  3. customevaporated under vacuum
  4. customThe residue was partitioned between DCM and water
  5. extractionextracted with DCM
  6. customevaporated onto silica
  7. customThe silica was deposited onto a 10 g silica cartridge and purification by chromatography on silica eluting with 10-50% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-d7d953edf53a4e228498705318760fd7
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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