Water → 4-[2-(2-Methyl-4-pentylphenoxy)ethylamino]thieno[2,3-d]pyrimidine

HRID 638580Notes

Reaction equation

HRID 638580 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.[CH3:11][C:12]1[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:19]=[CH:18][C:13]=1[O:14][CH2:15][CH2:16][NH2:17].C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[CH3:11][C:12]1[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:19]=[CH:18][C:13]=1[O:14][CH2:15][CH2:16][NH:17][C:2]1[C:3]2[CH:10]=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 7366184-Chlorothieno[2,3-d]pyrimidineHCID 155880312-(2-Methyl-4-pentylphenoxy)ethylamine

Product 1

HCID 133431904-[2-(2-Methyl-4-pentylphenoxy)ethylamino]thieno[2,3-d]pyrimidineYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.4 g (0.02 mole) of 4-chlorothieno[2,3-d]pyrimidine, 4.4 g (0.02 mole) of 2-(2-methyl-4-pentylphenoxy)ethylamine and 2 g (0.02 mole) of triethylamine were dissolved in 50 ml of toluene, and the solution was heated under reflux for 4 hours. At the end of this time, water was added to the reaction mixture, and the mixture was then extracted with toluene. The extract was dried over anhydrous sodium sulphate, and the solvent was distilled off, after which the residue was recrystallised from a mixture of toluene and hexane, to give 5.4 g (yield 76%) of the title compound in the form of colourless crystals melting at 93°-95° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 4 hours
  3. extractionthe mixture was then extracted with toluene
  4. dry with materialThe extract was dried over anhydrous sodium sulphate
  5. distillationthe solvent was distilled off
  6. customafter which the residue was recrystallised from a mixture of toluene and hexane

Sources & evidence

ORD record
ord-0ae162c335404a32b5759b13682389a7
Source dataset
uspto-grants-1985_12
Patent number
US04562193

Reaction notes

Loading…