Dimethylformamide → 4-(6-iodo-1H-indazol-1-yl)pyrimidine-2,5-diamine

HRID 1398494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398494
[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[C:11]2[C:16]([N+:17]([O-])=O)=[CH:15][N:14]=[C:13]([NH2:20])[N:12]=2)=[CH:4][CH:3]=1.CN(C=O)C.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>CO.O>[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[C:11]2[C:16]([NH2:17])=[CH:15][N:14]=[C:13]([NH2:20])[N:12]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 681819814-(6-iodo-1H-indazol-1-yl)-5-nitropyrimidin-2-amine2×

Produkt 1

HCID 681817304-(6-iodo-1H-indazol-1-yl)pyrimidine-2,5-diamineAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of 4-(6-iodo-1H-indazol-1-yl)-5-nitropyrimidin-2-amine (200 mg, 45% purity, 0.236 mmol) in a mixture of methanol (4 mL), DMF (3 mL) and water (3 mL) was added sodium dithionite (205 mg, 1.178 mmol) and sodium bicarbonate (99 mg, 1.178 mmol). The suspension was stirred at RT for 2 hr. After 2 hr LC-MS (Method B) showed 11% of desired product, 15% of starting 4-(6-iodo-1H-indazol-1-yl)-5-nitropyrimidin-2-amine (16-a) and 67% of degraded by-product. The reaction mixture was diluted with EtOAc (30 mL) and washed with water (2×10 mL), then dried over Na2SO4, filtered and concentrated in vacuo to give the crude title compound; m/z=+352.9 (M+H)+, (purity=11%). This intermediate was used in the next step without further purification.

Aufarbeitung

  1. waitAfter 2 hr LC-MS (Method B) showed

Quellen und Nachweise

ORD-Eintrag
ord-1ae29d298f844cc2b73c8113f1d4e13e
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901313B2

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