Sodium Hydroxide → 2-Amino-4-phenyl-thieno[2,3-d]pyrimidine-6-carboxylic acid

HRID 237373Notes

Reaction equation

HRID 237373 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[S:23][C:11]2[N:12]=[C:13]([NH2:22])[N:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]=2[CH:9]=1)=[O:7])C>C(O)C.O>[NH2:22][C:13]1[N:14]=[C:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]2[CH:9]=[C:8]([C:6]([OH:7])=[O:5])[S:23][C:11]=2[N:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11255023Ethyl 2-amino-4-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 113802352-Amino-4-phenyl-thieno[2,3-d]pyrimidine-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium Hydroxide (0.66 g; 16.5 mmol) was added to a suspension of 2-amino-4-phenyl-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (Example 1) (1.00 g; 3.34 mmol) in ethanol (20 ml) and water (2 ml). The mixture was heated at reflux for 1 hour (affording a homogeneous pale-yellow solution) and allowed to cool to ambient temperature. Solvents were removed in vacuo and the solid residue was dissolved in water (30 mL) and cooled with ice-water bath. The mixture was stirred and adjusted to pH 1-2 by drop-wise addition of concentrated Hydrochloric acid. The resulting precipitate was filtered, washed with water, then ethanol and finally diethyl ether. The off-white product was dried in vacuo to afford 2-amino-4-phenyl-thieno[2,3-d]pyrimidine-6-carboxylic acid as a colourless solid (0.784 g; 87%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour (
  3. customaffording a homogeneous pale-yellow solution) and
  4. customSolvents were removed in vacuo
  5. dissolutionthe solid residue was dissolved in water (30 mL)
  6. temperaturecooled with ice-water bath
  7. additionadjusted to pH 1-2 by drop-wise addition of concentrated Hydrochloric acid
  8. filtrationThe resulting precipitate was filtered
  9. washwashed with water
  10. customThe off-white product was dried in vacuo

Sources & evidence

ORD record
ord-6bd0b034f72f43ddb6fd79eda178d8e3
Source dataset
uspto-grants-2014_02
Patent number
US08642594B2

Reaction notes

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