Water → HCID 13343193, compound

HRID 638581Notes

Reaction equation

HRID 638581 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:11]([C:14]1[CH:23]=[CH:22][C:17]([O:18][CH2:19][CH2:20][NH2:21])=[C:16]([CH3:24])[CH:15]=1)[CH:12]=[CH2:13].C(N(CC)CC)C.O>C1C=CC=CC=1>[CH2:11]([C:14]1[CH:23]=[CH:22][C:17]([O:18][CH2:19][CH2:20][NH:21][C:2]2[C:3]3[CH:10]=[CH:9][S:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[C:16]([CH3:24])[CH:15]=1)[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 7366184-Chlorothieno[2,3-d]pyrimidineHCID 19789879HCID 19789879, compound

Product 1

HCID 13343193HCID 13343193, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3.4 g (0.02 mole) of 4-chlorothieno[2,3-d]pyrimidine, 3.8 g (0.02 mole) of 2-(4-allyl-2-methylphenoxy)ethylamine and 2 g (0.02 mole) of triethylamine were dissolved in 50 ml of benzene, and the solution was heated under reflux for 6 hours. At the end of this time, water was added to the reaction mixture, after which it was extracted with benzene. The extract was dried over anhydrous sodium sulphate and the solvent was distilled off, after which the residue was subjected to column chromatography through silica gel, eluted with a 9:1 by volume mixture of benzene and ethyl acetate, to give 5.4 g (yield 83%) of the desired Compound No. 8, in the form of pale yellow crystals melting at 97°-99° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 6 hours
  3. extractionafter which it was extracted with benzene
  4. dry with materialThe extract was dried over anhydrous sodium sulphate
  5. distillationthe solvent was distilled off
  6. washeluted with a 9:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-a87d2909cf4345b2aa7d3e4843f0b6ed
Source dataset
uspto-grants-1985_12
Patent number
US04562193

Reaction notes

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