Triethylamine → HCID 89579974, compound

HRID 928608Notes

Reaction equation

HRID 928608 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.Cl[C:10]1[C:11]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:19][S:18][C:12]=2[N:13]=[C:14]([CH2:16][Cl:17])[N:15]=1.C(N(CC)CC)C>C(O)C>[Cl:17][CH2:16][C:14]1[N:15]=[C:10]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]2)[C:11]2[C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:19][S:18][C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4207714-PiperidinemethanolHCID 23726818HCID 23726818, compound

Product 1

HCID 89579974HCID 89579974, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Piperidinemethanol (0.85 g) was added to a suspension of 4-chloro-2-(chloromethyl)-5-phenyl-thieno[2,3-d]pyrimidine (1.45 g) in ethanol (70 mL). Triethylamine (1.4 mL) was added and the mixture was stirred at room temperature for 24 hr. The solvent was evaporated and the residue was dissolved in water (100 mL) and ethyl acetate (100 mL). The layers were separated and the aqueous was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (1×100 mL), dried (sodium sulfate), filtered and evaporated to give an off-white foam (1.76 g). This was purified by silica chromatography (50 g cartridge; eluent petroleum ether 40-60/ethyl acetate 0 to 50%; collection by UV trigger). Fractions corresponding to the main peak were combined and evaporated to give the target compound as a white foam (1.10 g). m/z [M+H]+373.9/375.9. Retention time 4.67 min (LCMS method+ve 6 min).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water (100 mL)
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with ethyl acetate (2×100 mL)
  5. washThe combined organic layers were washed with brine (1×100 mL)
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-b03b6fbd4bfa42a4b744312720d82546
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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