ChemicalBook CAS DataBase List 5-Bromo-2-methyl-4-pyrimidinecarboxylic acid

5-Bromo-2-methyl-4-pyrimidinecarboxylic acid synthesis

3synthesis methods

Product Name:5-Bromo-2-methyl-4-pyrimidinecarboxylic acid
CAS Number:100707-39-9
Molecular formula:C6H5BrN2O2
Molecular Weight:217.02

766-38-1
23 suppliers
$176.22/1g

124-42-5 Synthesis

124-42-5
356 suppliers
$6.00/25g

5-Bromo-2-methyl-4-pyrimidinecarboxylic acid

100707-39-9
129 suppliers
$18.00/100mg

Yield:100707-39-9 42%

Reaction Conditions:

Stage #1: acetamidine hydrochloridewith sodium ethanolate in ethanol at 50;
Stage #2: mucobromic acidwith sodium ethanolate in ethanol;

Steps:

42.42a

Step 42a: 5-Bromo-2-methylpyrimidine (Compound 0601-120)Sodium (356 mg, 15.5 mmol) was carefully added to ethanol (5.9 mL) to prepare sodium ethoxide solution in ethanol. The above freshly prepared sodium ethoxide in ethanol solution (3.5 mL) was added to a stirred suspension of acetamidine hydrochloride (0.91 g, 9.69 mmol). The mixture was warmed to 50 °C, then the heating bath was removed and a solution of mucobromic acid (1 g, 3.87 mmol) in ethanol was added dropwise at a rate which maintained a constant temperature, followed by a further sodium ethoxide in ethanol solution (2 mL). After cooling, the mixture was filtered and evaporated to a residue which was shaken vigorously with hydrochloric acid (2 M x 2.4 mL). The brown precipitate was filtered and washed with cold water, then freeze-dried to give 5-bromo-2- methylpyrimidine-4-carboxylic acid (350 mg, 42%) as a brown solid. LCMS: 218 [M+l]⁺, 1H NMR (400 MHz, DMSO-d₆): δ 2.62 (s, 3H), 9.03 (s, 1H).

References:

WO2011/130628,2011,A1 Location in patent:Page/Page column 176

90994-06-2 Synthesis