Sodium Hydroxide → 4-(4-Fluoro-2-((tetrahydro-2-H-pyran-4-yl)methoxy)phenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid

HRID 532290Notes

Reaction equation

HRID 532290 reaction equation
C[O:2][C:3]([C:5]1[S:29][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][CH2:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:7]=2[C:6]=1[CH3:30])=[O:4].[OH-].[Na+]>C(O)C.ClCCl.Cl>[F:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:12]2[C:7]3[C:6]([CH3:30])=[C:5]([C:3]([OH:4])=[O:2])[S:29][C:8]=3[N:9]=[CH:10][N:11]=2)=[C:15]([O:21][CH2:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:16]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 58413397Methyl-4-(4-fluoro-2-((tetrahydro-2-H-pyran-4-yl)methoxy)phenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 584133504-(4-Fluoro-2-((tetrahydro-2-H-pyran-4-yl)methoxy)phenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl-4-(4-fluoro-2-((tetrahydro-2-H-pyran-4-yl)methoxy)phenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (82 mg) and NaOH (2M; 0.5 ml) was dissolved in ethanol (2 ml). The reaction was stirred at room temperature overnight. Then the reaction mixture was diluted with dichloromethane and HCl (2M). The suspension was filtered, washed with brine and ether. The residue was dried in vacuo over P2O5.

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with brine and ether
  3. dry with materialThe residue was dried in vacuo over P2O5

Sources & evidence

ORD record
ord-ddeaacbfc298488796da70ee55d7cc81
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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