Hydrochloric Acid → 4-(4-Fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylic acid

HRID 450534Notes

Reaction equation

HRID 450534 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[C:17]([CH3:18])=[C:16]([C:19]([O:21]C)=[O:20])[S:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[C:4]([O:23][CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:3]=1.O.[OH-].[Li+].Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[C:17]([CH3:18])=[C:16]([C:19]([OH:21])=[O:20])[S:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[C:4]([O:23][CH:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 461820444-[4-Fluoro-2-(tetrahydro-pyran-4-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methylester

Product 1

HCID 461826634-(4-Fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylic acidYield 99.2%

Reagents, catalysts & solvents 1

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

Procedure

Methyl 4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (9.0 g, 21.6 mmol) was suspended in THF/water (1:1; 200 mL). Into this solution was added lithium hydroxide monohydrate (5.31 g, 126.5 mmol) and the reaction stirred at ambient temperature overnight. The solution was cooled in an ice-bath and concentrated hydrochloric acid added until the solution reached pH 4. The precipitate was collected, washed with water and dried over P2O5 to yield off-white solid (8.642 g, 99%).

Workup

  1. temperatureThe solution 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-47c28839f1634a4780bb1c8c2e35f14e
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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