p-Toluenesulfonic acid → Methyl 4-(4-fluoro-2-hydroxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate

HRID 240598Notes

Reaction equation

HRID 240598 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:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[OH:24].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH4+].[OH-]>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[OH:24])[C:7]=2[C:6]=1[CH3:15])=[O:4]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 14923Ammonium HydroxideHCID 1857632-Amino-5-fluorophenolHCID 2759834Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 58413076Methyl 4-(4-fluoro-2-hydroxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (2.43 g), 2-amino-5-fluorophenol (2.43 g) and p-toluenesulfonic acid (190.0 mg) were dissolved in dioxane (50.0 ml) and heated at 120° C. for 4 h under nitrogen. The reaction mixture was allowed to cool and treated with 3M NH4OH. The resultant suspension was filtered, the solid was washed with ether and dried in vacuo at 60° C. over P2O5.

Workup

  1. temperatureto cool
  2. filtrationThe resultant suspension was filtered
  3. washthe solid was washed with ether
  4. dry with materialdried in vacuo at 60° C. over P2O5

Sources & evidence

ORD record
ord-cf324c23c5ed405093e176a4ce654e97
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

Loading…