DR ANTHONY MELVIN CRASTO,WorldDrugTracker, helping millions, A 90 % paralysed man in action for you, I am suffering from transverse mylitis and bound to a wheel chair, With death on the horizon, nothing will not stop me except God................DR ANTHONY MELVIN CRASTO Ph.D ( ICT, Mumbai) , INDIA 25Yrs Exp. in the feld of Organic Chemistry,Working for GLENMARK GENERICS at Navi Mumbai, INDIA. Serving chemists around the world. Helping them with websites on Chemistry.Million hits on google, world acclamation from industry, academia, drug authorities for websites, blogs and educational contribution
Showing posts with label (5. Show all posts
Showing posts with label (5. Show all posts

Tuesday 24 February 2015

(5,7-Dimethyl-4,6-dioxo-4,5,6,7-tetrahydro[1,2]thiazolo[3,4-(/]pyrimidin-3- yl)acetic acid

(5,7-Dimethyl-4,6-dioxo-4,5,6,7-tetrahydro[1,2]thiazolo[3,4-(i]pyrimidin-3-yl)acetic acid
Figure imgf000024_0002


Step 1 : Methyl 6-amino-l,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5- carbodithioate: 
1H NMR (300 MHz, CF3COOD) δ 2.73 (s, 3H), 3.51 (s, 3H), 3.62 (s, 3H).

Step 2: 5,7-Dimethyl-3-(methylsulfanyl)[1,2]thiazolo[3,4-ύT|pyrimidine-4,6(5H,7H)- dione: 
1H NMR (300 MHz, DMSO-^6) δ 2.67 (s, 3H), 3.18 (s, 3H), 3.40 (s, 3H). 

Step 3: 5,7-Dimethyl-3-(methylsulfonyl)[1,2]thiazolo[3,4-(/]pyrimidine-4,6(5H,7H)- dione:  
 1H NMR (300 MHz, DMSO-(Z6) δ 3.26 (s, 3H), 3.49 (s, 3H), 3.71 (s, 3H).

Step 4: Diethyl (5,7-dimethyl-4,6-dioxo-4,5,6,7-tetrahydro[1,2]thiazolo[3,4-d]pyrimidin- 3-yl)propanedioate:  1H NMR (300 MHz, DMSO-(Z6) δ 1.32 (t, J = 7.2 Hz, 6H), 3.40 (s, 3H), 3.64 (s, 3H), 4.24-4.37 (m, 4H), 6.05 (s, 1H).


Step 5: Ethyl (5,7-dimethyl-4,6-dioxo-4,5,6,7-tetrahydro[1,2]thiazolo[3,4-d]pyrimidin-3- yl)acetate:; 1H NMR (300 MHz, DMSCM6) δ 1.34 (t, J = 6.9 Hz, 3H), 3.40 (s, 3H), 3.63 (s, 3H), 4.30 (q, J= 6.9 Hz, 2H), 4.50 (s, 2H)


Step 6: (5,7-Dimethyl-4,6-dioxo-4,5,6,7-tetrahydro[1,2]thiazolo[3,4-(/]pyrimidin-3- yl)acetic acid: The title compound was prepared according to same procedure as described for Intermediate 1, Step 5 by using above Step 5 intermediate (9.0 g, 31.8 mmol), 6 N H2SO4 (80 ml) and dioxane (80 ml) to give 5.8 g of the product as yellow solid; 

 1H NMR (300 MHz, DMSO-^6)
δ 3.22 (s, 3H),
3.46 (s, 3H),
4.51 (s, 2H),
13.45 (br s, 1H).  -0H

Interpretation

 

http://www.google.com/patents/EP2411397A1?cl=en 



(5,7-Dimethyl-4,6-dioxo-4,5,6,7-tetrahydro[1,2]thiazolo[5,4-(i]pyrimidin-3-yl)acetic acid
Figure imgf000026_0001 

1H NMR (300 MHz, DMSO-<4) δ 3.22 (s, 3H), 3.46 (s, 3H), 3.96 (s, 2H), 12.57 (br s, 1H).


2-(5,7-Dimethyl-4,6-dioxo-4,5,6,7-tetrahydro[1,2]thiazolo[3,4-ύT|pyrimidin-3-yl)-N-{4- [3 -fluoro-4-(trifluoromethyl)phenyl] - 1 ,3 -thiazol-2-yl } acetamide
Figure imgf000034_0001
 1H ΝMR (300 MHz, DMSO-^6) δ 3.23 (s, 3H), 3.48 (s, 3H), 4.83 (s, 2H), 7.86-8.07 (m, 4H), 12.96 (br s, 1H); APCI-MS (m/z) 500.06 (M+H)+.





2-(5,7-Dimethyl-4,6-dioxo-4,5,6,7-tetrahydro[1,2]thiazolo[3,4-ύT|pyrimidin-3-yl)-N-{4- [3 -(trifluoromethy l)pheny 1] -1,3 -thiazol-2 -y 1 } acetamide
Figure imgf000033_0001
 1H NMR (300 MHz, DMSO-^6) δ 3.23 (s, 3H), 3.48 (s, 3H), 4.82 (s, 2H), 7.67- 7.72 (m, 2H), 7.96 (s, 1H), 8.20-8.26 (m, 2H), 12.93 (br s, 1H); APCI-MS (m/z) 482.07 (M+H)+.




Ethyl (5,7-dimethyl-4,6-dioxo-4,5,6,7-tetrahydro[1,2]thiazolo[5,4-ύT|pyrimidin-3- yl)acetate
 1H NMR (300 MHz, CDCl3
δ 1.28 (t, J= 7.2 Hz, 3H), -CH2CH3
3.39 (s, 3H), 
3.56 (s, 3H), 
4.12 (s, 2H), -CH2CH3
4.21 (q, J= 6.9 Hz, 2H).


Figure imgf000027_0001




Figure imgf000029_0001


Figure imgf000030_0001