Ethylene Glycol → HCID 69070807, compound

HRID 2066938Notes

Reaction equation

HRID 2066938 reaction equation
Cl[CH2:2][C:3]1[NH:4][C:5](=[O:18])[C:6]2[C:11]([CH3:12])=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:9][C:7]=2[N:8]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(O)CO.C(N(CC)CC)C>O>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][N:29]([CH2:2][C:3]2[NH:4][C:5](=[O:18])[C:6]3[C:11]([CH3:12])=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:9][C:7]=3[N:8]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2339310Ethyl 2-(chloromethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 69070807HCID 69070807, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.15 g of ethyl 2-chloromethyl-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate, 745 mg of tert-butoxycarbonylpiperazine, 20 mL of ethylene glycol and 400 mg of triethylamine was stirred at 80° C. for 3 hours. Thereafter water was added to the reaction mixture, followed by extraction with chloroform, drying over anhydrous magnesium sulfate, and removal of the solvent by distillation under reduced pressure. The residue was purified on silica gel column chromatography (ethyl acetate:chloroform:hexane=2:1:1) to provide 1.36 g (78%) of the title compound.

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialdrying over anhydrous magnesium sulfate, and removal of the solvent by distillation under reduced pressure
  3. customThe residue was purified on silica gel column chromatography (ethyl acetate:chloroform:hexane=2:1:1)

Sources & evidence

ORD record
ord-803c54cd0c834d5b9c09f045e276f858
Source dataset
uspto-grants-2012_10
Patent number
US08293754B2

Reaction notes

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