Hydrochloric Acid → 7-Amino-2-chlorothiazolo[4,5-d]pyrimidine

HRID 1638533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1638533
N[C:2]1[S:3][C:4]2[C:9]([NH2:10])=[N:8][CH:7]=[N:6][C:5]=2[N:11]=1.[OH-].[Na+].N([O-])=O.[Na+].[ClH:18].[Li+].[Cl-]>O>[NH2:10][C:9]1[C:4]2[S:3][C:2]([Cl:18])=[N:11][C:5]=2[N:6]=[CH:7][N:8]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 433294Lithium ChlorideHCID 10953913Thiazolo[4,5-d]pyrimidine-2,7-diamineHCID 23668193Sodium Nitrite

Produkt 1

HCID 145057597-Amino-2-chlorothiazolo[4,5-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a suspension of 2,7-diaminothiazolo[4,5-d]pyrimidine (27: 16.3 g, 97.3 mmol) in water (200 mL) at 55° C. was added enough 1N NaOH (about 100 mL) to dissolve the starting material and sodium nitrite (8.0 g) was then added. This solution was then added dropwise over 30 min. to a solution containing con HCl (400 mL), water (100 mL) and LiCl (60 g) at 30° C. The resulting mixture was warmed to 45° C. for 15 min. and then hot water (1 L, 90°) was added. The reaction mixture was stirred overnight at room temperature, filtered to remove unreacted starting material and the filtrate was neutralized with solid NaOH to pH 4. The resulting solid was filtered off, washed with water and dried to yield 28: 5.38 g, 34%: recrystallization from water gave an analytical sample- mp >234° C. decomp.: UV λmax (pH 1) 228 nm (ε), 296 (): UV λmax (pH 7) 232 nm (ε), 298 (): UV λmax (pH 119 227 nm (ε), 300 (): 1H NMR (DMSO-d6) δ7.82 (b, 2H, NH2, exchanges with D2O), 8.41 (s, 1H, C5H). Anal. Calcd. for C5H3N4SCl.0.1H2O: C, 31.87: H, 1.71: N, 29.74: S, 17.02: Cl, 18.82. Found: C, 31.71: H, 1.50: N, 29.35: S, 16.92: Cl, 19.54.

Aufarbeitung

  1. additionwas then added
  2. additionThis solution was then added dropwise over 30 min. to a solution
  3. filtrationfiltered
  4. customto remove unreacted
  5. filtrationThe resulting solid was filtered off
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a228ee3d394c49b0bed9ee9d8d3ef051
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04880784

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