Triethylamine → HCID 22272654, compound

HRID 1064802Notes

Reaction equation

HRID 1064802 reaction equation
C(N(CC)CC)C.[CH3:8][S:9][C:10]1[C:15]([NH2:16])=[C:14]([S:17][CH3:18])[N:13]=[CH:12][N:11]=1.[Br:19][CH2:20][C:21](Br)=[O:22]>C1COCC1.O>[CH3:18][S:17][C:14]1[C:15]([NH:16][C:21](=[O:22])[CH2:20][Br:19])=[C:10]([S:9][CH3:8])[N:11]=[CH:12][N:13]=1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 61147Bromoacetyl bromide2×HCID 2387334,6-bis(methylthio)-5-aminopyrimidine

Product 1

HCID 22272654HCID 22272654, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (78 mg, 0.8 mmol) was added to a solution of 4,6-bis(methylthio)-5-aminopyrimidine (120 mg, 0.7 mmol) in THF (2 ml) at room temperature, then bromoacetyl bromide (141 mg, 0.7 mmol) was dropped thereinto and the mixture was stirred for 1 hour. Then the same amounts of triethylamine and bromoacetyl bromide were added followed by stirring for 1 hour. The reaction solution was diluted with water and extracted with ether. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over magnesium sulfate and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (20 g of silica gel; developing solvent, hexane:acetone=5:1) to provide 78 mg (yield 40%) of N-[4,6-bis(methylthio)-5-pyrimidyl]-2-bromoacetamide as pale yellow crystals.

Workup

  1. stirringby stirring for 1 hour
  2. extractionextracted with ether
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution successively and dried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by a silica gel column chromatography (20 g of silica gel; developing solvent, hexane:acetone=5:1)

Sources & evidence

ORD record
ord-9e7df0de329546958a188bfd48600ba6
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

Loading…