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

HRID 1773614Notes

Reaction equation

HRID 1773614 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+]>O1CCCC1.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

9

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 95.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent3×HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 0.640 g (3.22 mmole) 2-chloro-thieno[3,2-d]pyrimidine-7-carbaldehyde in 20 mL of tetrahydrofuran, 10 mL of tert-butanol and 10 mL of water was added 1.25 g (12.9 mmole) of sulfamic acid. A solution of 0.729 g (8.06 mmole) sodium chlorite and 3.33 g (24.5 mmole) of potassium dihydrogen phosphate in 24 mL of water was slowly added via additional funnel. The reaction mixture was stirred at room temperature for over night. Water and ethyl acetate were added, separated. Aqueous layer was washed with ethyl acetate. Organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The solid residue was dried in high vacuum for over night to give 0.660 g of 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid as a yellow solid. MH+/Z=215

Workup

  1. customseparated
  2. washAqueous layer was washed with ethyl acetate
  3. washOrganic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe solid residue was dried in high vacuum for over night

Sources & evidence

ORD record
ord-b5b0f64bfc14409abdac2d1ae3cba851
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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