Trifluoroacetic acid → Ethyl 6-ethyl-3,4-dihydro-5-hydroxy-4-oxothieno[2,3-d]PYRIMIDINE-2-CARBOXYLATE

HRID 973044Notes

Reaction equation

HRID 973044 reaction equation
N[C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:6][C:5]=2[S:4][C:3]=1[CH2:17][CH3:18].[B-](F)(F)(F)F.FC(F)(F)C([O-])=[O:27].[K+].FC(F)(F)C(O)=O>>[CH2:17]([C:3]1[S:4][C:5]2[N:6]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:8][C:9](=[O:11])[C:10]=2[C:2]=1[OH:27])[CH3:18]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 26255TetrafluoroborateHCID 12516925Ethyl 5-amino-6-ethyl-3,4-dihydro-4-oxothieno[2,3-d]PYRIMIDINE-2-CARBOXYLATEHCID 23662811Potassium trifluoroacetate

Product 1

HCID 23330393Ethyl 6-ethyl-3,4-dihydro-5-hydroxy-4-oxothieno[2,3-d]PYRIMIDINE-2-CARBOXYLATE

Conditions

Temperature
25 °C

Procedure

The diazonium fluoroborate salt is prepared as in Procedure 63 from the amino compound produced in Procedure 51 yielding 0.03 mole of the required idazonium fluoborate. The latter is added in one portion to a solution of 0.03 mole of potassium trifluoroacetate in 13 ml. of trifluoroacetic acid at 0° C. The mixture is stirred at 25° C. for 1 hour and then refluxed overnight. The trifluoroacetic acid is evaporated in vacuo to give a residue which is triturated with water and filtered to give the desired product.

Workup

  1. customat 0° C
  2. temperaturerefluxed overnight
  3. customThe trifluoroacetic acid is evaporated in vacuo
  4. customto give a residue which
  5. customis triturated with water
  6. filtrationfiltered

Sources & evidence

ORD record
ord-2d90e88b0aae47a48537ed6a9b4507da
Source dataset
uspto-grants-1977_10
Patent number
US04054656

Reaction notes

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