Triethylamine → HCID 86723513, compound

HRID 2201275Notes

Reaction equation

HRID 2201275 reaction equation
[NH2:1][C@H:2]([CH2:5][S:6][C:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4].C(N(CC)CC)C.[C:33]([C:41]1[C:42](=[O:52])[N:43]([CH3:51])[C:44](=[O:50])[N:45]([CH3:49])[C:46]=1[CH2:47]Br)(=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CCO>[OH:4][CH2:3][C@H:2]([N:1]1[C:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:41]2[C:46]([N:45]([CH3:49])[C:44](=[O:50])[N:43]([CH3:51])[C:42]2=[O:52])=[CH:47]1)[CH2:5][S:6][C:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione2×HCID 71502325HCID 71502325, compound

Product 1

HCID 86723513HCID 86723513, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-2-Amino-3-(tritylthio)propan-1-ol (step 1) (1.58 g, 4.52 mmol), triethylamine (1.454 mL, 10.43 mmol) and 5-benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (Intermediate C) (1.173 g, 3.48 mmol) were combined in EtOH (60 mL) and the mixture heated at reflux for 1 hour. The reaction mixture was cooled to RT and evaporated under vacuum. The residue was partitioned between DCM and water and the phases separated. The organic phase was passed through a hydrophobic frit and evaporated under vacuum to give the title compound which was used without further purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 hour
  3. customevaporated under vacuum
  4. customThe residue was partitioned between DCM and water
  5. customthe phases separated
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-13ad5aa647324e0184e30a1c435b81ff
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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