p-Toluenesulfonic acid → HCID 58413084, compound

HRID 240641Notes

Reaction equation

HRID 240641 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].[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([O:24][C@@H:25]2[CH2:29][CH2:28][O:27][CH2:26]2)[CH:18]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][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:19]([O:24][C@@H:25]2[CH2:29][CH2:28][O:27][CH2:26]2)[CH:18]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 2759834Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylateHCID 58413003HCID 58413003, compound2×

Product 1

HCID 58413084HCID 58413084, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (100 mg) and (R)-4-fluoro-2-(tetrahydrofuran-3-yloxy)aniline (Intermediate VI) (81 mg) was dissolved in Dioxan (2 ml) and p-Toluenesulfonic acid (15 mg) was added. The reaction heated at 110° C. under microwave radiation. The resultant precipitate was filtered and dissolved in dichloromethane/Methanol. The solution was dried and concentrated to give the desired product.

Workup

  1. filtrationThe resultant precipitate was filtered
  2. dissolutiondissolved in dichloromethane/Methanol
  3. customThe solution was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3f086e8cb96f41078ad73c5583f84926
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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