Methyl 2-amino-3-thenoate → thieno[2,3-d]pyrimidine-2,4-diol

HRID 736315Notes

Reaction equation

HRID 736315 reaction equation
CO[C:3]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[NH2:10])=[O:4].[O-:11][C:12]#[N:13].[K+]>C(O)(=O)C.O>[NH:10]1[C:6]2[S:7][CH:8]=[CH:9][C:5]=2[C:3](=[O:4])[NH:13][C:12]1=[O:11]

Participants

5

Reactant 2

HCID 78381Methyl 2-amino-3-thenoateHCID 11378442Potassium cyanate

Product 1

HCID 12217323thieno[2,3-d]pyrimidine-2,4-diolYield 25.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of methyl-2-aminothiophene-3-carboxylate (2.03 g, 12.9 mmol) in acetic acid (65 mL) and water (6.5 mL) was added a solution of potassium cyanate (3.14 g, 38.7 mmol) dissolved in water (10.4 mL) dropwise via syringe. The reaction was stirred at room temperature for 15 h, upon completion of the reaction; the reaction mixture was concentrated to 75% and filtered off white solid. To the solid was added 6% aqueous sodium hydroxide (16 mL) and refluxed for 2 h. After cooling to room temperature, the solution was acidified using 12N HCl to pH=6. The resultant precipitate was filtered, washed with water and dried in a vacuum oven overnight to give 546 mg (25%) of the title compound as an orange solid which was used without any further purification:

Workup

  1. concentrationthe reaction mixture was concentrated to 75%
  2. filtrationfiltered off white solid
  3. additionTo the solid was added 6% aqueous sodium hydroxide (16 mL)
  4. temperaturerefluxed for 2 h
  5. temperatureAfter cooling to room temperature
  6. filtrationThe resultant precipitate was filtered
  7. washwashed with water
  8. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-33bd7d78097b4b1381695bca38c51536
Source dataset
uspto-grants-2009_09
Patent number
US07595324B2

Reaction notes

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