Sulfamic Acid → 2-Chlorothieno[3,2-D]pyrimidine-7-carboxylic acid

HRID 1773516Notes

Reaction equation

HRID 1773516 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([CH:11]=[O:12])[C:6]=2[N:7]=1.S(=O)(=O)([OH:15])N.Cl([O-])=O.[Na+].P([O-])(O)(O)=O.[K+]>C(O)(C)(C)C.O.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]([OH:15])=[O:12])[C:6]=2[N:7]=1

Participants

8

Reactant 4

HCID 5987Sulfamic AcidHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 717419452-Chlorothieno[3,2-D]pyrimidine-7-carbaldehyde

Product 1

HCID 580563052-Chlorothieno[3,2-D]pyrimidine-7-carboxylic acidYield 77.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-thieno[3,2-d]pyrimidine-7-carbaldehyde (0.6 g) in a mixture of tert-butanol/tertrahydrofuran/water (1/1/1, 45 mL) was added sulfamic acid (1.0 g) followed by a solution of sodium chlorite (0.9 g) and potassium dihydrogen phosphate (3.0 g) in water (10 mL) and the resulting mixture was stirred for 1 hour. The reaction mixture was then diluted with ethyl acetate; the organic layer was separated and washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was triturated with ethyl acetate and the solid was collected by filtration to give 0.5 g of 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid.

Workup

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was triturated with ethyl acetate
  7. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-23371432a76d4f038073721bb24eb4e2
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

Loading…