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

HRID 240653Notes

Reaction equation

HRID 240653 reaction equation
C[O:2][C:3]([C:5]1[S:28][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[O:21][CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[C:7]=2[C:6]=1[CH3:29])=[O:4].[OH-].[Li+].Cl>C1COCC1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:12]2[C:7]3[C:6]([CH3:29])=[C:5]([C:3]([OH:4])=[O:2])[S:28][C:8]=3[N:9]=[CH:10][N:11]=2)=[C:15]([O:21][CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 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 acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[4-Fluoro-2-(tetrahydro-pyran-4-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methylester (13.45 g) was dissolved in THF (100 ml) and lithium hydroxide (1M; 80.5 ml) was added. The reaction mixture was stirred at room temperature for 5 h. The mixture was acidified with HCl (1M) to pH 2, the resultant precipitate was filtered and washed with water.

Workup

  1. filtrationthe resultant precipitate was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-c6ca8b0f214a45fbbf79f0f9ba107964
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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