2,4-diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidine → 2,4-diamino-5-(7,8-dimethoxy-4H-1-benzopyran-5-ylmethyl)pyrimidine acetate

HRID 34463

Reaktionsgleichung

Reaktionsgleichung von HRID 34463
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[C:15]3[CH:16]=[CH:17][CH2:18][O:19][C:14]=3[C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=2)=[CH:4][N:3]=1.CC(C)([O-:27])C.[K+]>CS(C)=O.O>[C:18]([OH:19])(=[O:27])[CH3:17].[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[C:15]3[CH2:16][CH:17]=[CH:18][O:19][C:14]=3[C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=2)=[CH:4][N:3]=1

Komponenten

5

Edukt 2

HCID 128497722,4-diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 201298172,4-diamino-5-(7,8-dimethoxy-4H-1-benzopyran-5-ylmethyl)pyrimidine acetateAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2,4-Diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidine (3.35 g, 10.6 mmol) and potassium t-butoxide (2.5 g) were warmed in dimethyl sulfoxide (25 mL) at 80° for 1.5 hr. The mixture was diluted with water and filtered. Two fractional crystallizations from 10% acetic acid gave 92% pure 2,4-diamino-5-(7,8-dimethoxy-4H-1-benzopyran-5-ylmethyl)pyrimidine acetate (0.62 g, 18%). The NMR was consistent with the structure with an 8% impurity of 2,4-diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimdine acetate. Anal. calcd for C16H18N4O3.C2H4O2 : C, 57.75; H, 5.92; N, 14.96. Found: C, 57.68; H, 5.93; N, 14.96.

Aufarbeitung

  1. filtrationfiltered
  2. customTwo fractional crystallizations from 10% acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-7d3e2b32fabc46818d509a1ab93a8af8
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761475

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