Dimethylformamide dimethyl acetal → N'-[7-(3-tert-butylureido)-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-2-yl]-N,N-dimethylformamidine

HRID 617963

Reaktionsgleichung

Reaktionsgleichung von HRID 617963
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9]([NH:20][C:21]([NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[N:8][C:6]=2[N:7]=1.[CH3:28][N:29]([CH:31](OC)OC)[CH3:30]>>[C:24]([NH:23][C:21](=[O:22])[NH:20][C:9]1[C:10]([C:12]2[C:13]([Cl:19])=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])=[CH:11][C:5]2[CH:4]=[N:3][C:2]([N:1]=[CH:28][N:29]([CH3:31])[CH3:30])=[N:7][C:6]=2[N:8]=1)([CH3:27])([CH3:26])[CH3:25]

Komponenten

3

Edukt 2

HCID 78373Dimethylformamide dimethyl acetalHCID 53281121-(2-Amino-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl)-3-(tert-butyl)urea

Produkt 1

HCID 54357764N'-[7-(3-tert-butylureido)-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-2-yl]-N,N-dimethylformamidine

Versuchsvorschrift

1-[2-Amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]-pyrimidin-7-yl]-3-tert-butylurea from Example 3 was reacted with DMF dimethyl acetal for 13.5 hours as described in Example 78. Workup as described above, followed by purification on flash silica gel chromatography eluting sequentially with 100:0, 3:1, 1:1, and 0:100 dichloromethane:ethyl acetate gave a solid that was triturated in 2-propanol to afford the title compound N'-[7-(3-tert-butylureido)-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-2-yl]-N,N-dimethylformamidine, mp 190-193° C. CIMS (1% ammonia in methane): m/z (relative intensity) 462 (MH+ +2, 0.78), 460 (MH+, 0.93).

Aufarbeitung

  1. customfollowed by purification on flash silica gel chromatography
  2. washeluting sequentially with 100:0, 3:1, 1:1, and 0:100 dichloromethane
  3. customethyl acetate gave a solid
  4. customthat was triturated in 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-989e38964ebf4387aab30202ff6d0348
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952342

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