Hydrochloric Acid → 4-(4-Fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)thieno[2,3-d]pyrimidine-6-carboxylic acid

HRID 450549Notes

Reaction equation

HRID 450549 reaction equation
O.[OH-].[Li+].[F:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]3[CH:20]=[C:19]([C:21]([O:23]C)=[O:22])[S:18][C:14]=3[N:15]=[CH:16][N:17]=2)=[C:7]([O:25][CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:6]=1.Cl>C1COCC1.O>[F:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]3[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[S:18][C:14]=3[N:15]=[CH:16][N:17]=2)=[C:7]([O:25][CH:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 46182082Methyl 4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)thieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 461820834-(4-Fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)thieno[2,3-d]pyrimidine-6-carboxylic acidYield 62%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide monohydrate (0.062 g, 1.49 mmol) was added into a suspension of methyl 4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)thieno[2,3-d]pyrimidine-6-carboxylate (0.100 g, 0.25 mmol) in THF/water (1:1; 1.0 mL) and the reaction stirred at ambient temperature for 16 hours. The mixture was cooled in an ice-bath and 1 N hydrochloric acid added drop wise until the solution reached pH 5. The precipitate was collected, washed with water and dried over P2O5 to yield off-white solid (0.060 g, 62%).

Workup

  1. temperatureThe mixture was cooled in an ice-bath
  2. customThe precipitate was collected
  3. washwashed with water
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-fb30df056e694a98a72e003b695c6e69
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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