p-Toluenesulfonic acid monohydrate → HCID 58413378, compound

HRID 532283Notes

Reaction equation

HRID 532283 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12](Cl)[C:7]=2[C:6]=1[CH3:15])=[O:4].[NH2:16][C:17]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:18]=1[O:19][CH:20]([CH3:26])[CH2:21][C:22]([CH3:25])([OH:24])[CH3:23].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[F:31][C:28]1[CH:29]=[CH:30][C:17]([NH:16][C:12]2[C:7]3[C:6]([CH3:15])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[S:14][C:8]=3[N:9]=[CH:10][N:11]=2)=[C:18]([O:19][CH:20]([CH2:21][C:22]([OH:24])([CH3:25])[CH3:23])[CH3:26])[CH:27]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 2759834Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylateHCID 58413264HCID 58413264, compound

Product 1

HCID 58413378HCID 58413378, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (540 mg) and 4-(2-amino-5-fluorophenoxy)-2-methylpentan-2-ol (500 mg) were dissolved in dioxane (20 ml) and p-toluenesulfonic acid monohydrate (70 mg) was added. The reaction was heated under reflux for 2 h. Then the reaction mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was dissolved in dichloromethane and washed with water. The organic layer was separated, dried, filtered and evaporated. The residue triturated with methanol and the precipitate was filtered to give the intended product.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 2 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water
  6. customThe organic layer was separated
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue triturated with methanol
  11. filtrationthe precipitate was filtered
  12. customto give the intended product

Sources & evidence

ORD record
ord-856053bc3ed0428d95fb16e973bd72bb
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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