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

HRID 1773516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773516
[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

Komponenten

8

Edukt 4

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

Produkt 1

HCID 580563052-Chlorothieno[3,2-D]pyrimidine-7-carboxylic acidAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6386tert-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-23371432a76d4f038073721bb24eb4e2
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255110B2

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