p-Toluenesulfonic acid → 6-Chloro-N-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-5-methylthieno[2,3-d]pyrimidin-4-amine

HRID 450585Notes

Reaction equation

HRID 450585 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:3]=1.Cl[C:17]1[C:18]2[C:25]([CH3:26])=[C:24]([Cl:27])[S:23][C:19]=2[N:20]=[CH:21][N:22]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[OH-].[NH4+]>O1CCOCC1.O>[Cl:27][C:24]1[S:23][C:19]2[N:20]=[CH:21][N:22]=[C:17]([NH:6][C:5]3[CH:7]=[CH:8][C:2]([F:1])=[CH:3][C:4]=3[O:9][CH:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:18]=2[C:25]=1[CH3:26]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 122252634,6-Dichloro-5-methylthieno[2,3-d]pyrimidineHCID 584130794-Fluoro-2-(oxan-4-yloxy)anilineHCID 86589665Water ammonium hydroxide

Product 1

HCID 461822996-Chloro-N-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-5-methylthieno[2,3-d]pyrimidin-4-amineYield 11.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Fluoro-2-(tetrahydro-2H-pyran-4-yloxy)aniline (0.057 g, 0.27 mmol), 4,6-dichloro-5-methylthieno[2,3-d]pyrimidine (0.06 g, 0.27 mmol, CA56844-14-5) and para-toluene sulfonic acid (0.005 g, 0.03 mmol) were heated at 90° C. in anhydrous 1,4-dioxane (1.5 mL) for 18 hours. The solution was cooled to ambient temperature, diluted with water (2 mL) and adjusted to pH 10 (4:1 water/ammonium hydroxide solution). The precipitate was collected, washed with water and diethyl ether to yield the title compound as yellow solid (0.012 g, 11%).

Workup

  1. customThe precipitate was collected
  2. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-4532c732f2e04d22b830ce8dc605f8e7
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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