5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid

White to yellow to light brown solid

Mucobromic acid (58.05 g, 0.225 mol) was added to a stirred solution of 2-methyl-2-thio- pseudourea sulfate (62.66 g, 0.225 mol) in water (500 mL) at r.t. The suspension was cooled to 10 °C (ice bath) and triethylamine (94.1 mL, 0.675 mol) was added dropwise over 4 h. The reaction mixture was then left to stand at r.t. for 24 h. Activated carbon (Darco G-60) was added to the now dark red / brown solution and after stirring for 10 min the charcoal was filtered off. The filtrate was acidified with concentrated hydrochloric acid (50 mL) and the yellow precipitate was filtered off, washed with water (2 x 80 mL) and diethyl ether (2 x 100 mL), and then placed in a vacuum oven at 50 (Z)-2 , 3-d ibromo-4- oxobut-2-enoic acid (30 g, 0.116 mol) was added to a stirred solution of methyl carbamimidothioate sulfate (1.2) (32 g, 0.116 mol) in water (250 mL) at it The suspension was cooled to 10 °C (ice bath) and Et3N (48.6 mL, 0.349 mol) was addeddrop wise over 1 h. The reaction mixture was stirred at rt for 12 h. Activated carbon (10 g) was added to the now dark reddish solution and 10 mm later, the charcoal was filtered off. The filtrate was acidified with concentrated hydrochloric acid (25 mL) and the yellow precipitate was filtered off, washed with water (2 x 80 mL) and diethyl ether (2 x 100 mL), dried in vacuum to afford the title compound (13 g, 45percent yield) as a yellow solid. LC-MS:[M-H] 247.7.Mucobromic acid (300 g, 1.16 mol) was added to an aqueous solution (2.5 L) of 2-methyl-2-pseudothiourea sulfate (324 g, 1.16 mol) at room temperature. The resultant suspension was cooled to 0°C with stir, and triethylamine (486 mL, 3.49 mol) was added dropwise thereto over four hours. The resultant reaction mixture was stirred overnight, and the completion of the reaction was confirmed by silica gel TLC. The reaction mixture was then acidified with concentrated hydrochloric acid (about 250 mL). The resultant yellow solid was collected by filtration and washed twice with water (500 mL) and then twice with diethyl ether (500 mL). The solid was dried under reduced pressure to yield the title compound (160 g, 55percent).

Molecular Weight:249.09
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:247.92551
Monoisotopic Mass:247.92551
Topological Polar Surface Area:88.4
Heavy Atom Count:12
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes