Hydrochloric Acid → 4-((4-Fluoro-2-isopropoxyphenyl)amino)-5-methylthieno(2,3-d)pyrimidine-6-carboxylic acid

HRID 532307Notes

Reaction equation

HRID 532307 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]([CH3:26])[CH3:25])[CH:3]=1.[OH-].[Li+].Cl>C1COCC1.CO.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]([CH3:26])[CH3:25])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 46182043Methyl 4-(4-fluoro-2-isopropoxyphenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 461826614-((4-Fluoro-2-isopropoxyphenyl)amino)-5-methylthieno(2,3-d)pyrimidine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Methyl 4-(4-fluoro-2-isopropoxyphenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate (451 mg) and lithium hydroxide (865 mg) was dissolved in a mixture of THF: methanol:water (1:1:1; 100 ml) and was stirred at room temperatruer overnight. Then the mixture was acidified with conc. HCl, the resultant precipitate was filtered, dried and triturated with diisopropyl ether to afford the title compound.

Workup

  1. filtrationthe resultant precipitate was filtered
  2. customdried
  3. customtriturated with diisopropyl ether

Sources & evidence

ORD record
ord-2d30aea08aee42bb814d76ae0a01fcab
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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