Methyl 2,4-dimethoxy-5-pyrimidinecarboxylate

To a suspension of 2, 4-Bis(methyloxy)-5-pyrimidinecarboxylic acid (Prep31 , 1.000 g, 5.43 mmol) in N, N-Dimethylformamide (DMF) (35 ml.) at 0 0C N, N'-Carbonyldiimidazole (1.321 g, 8.15 mmol) was added and the mixture was stirred for 1 hour at 0 0C, then left stirring at rt. After 4 h Triethylamine (2.271 ml_, 16.29 mmol) and N, N'-Carbonyldiimidazole (1.321 g, 8.15 mmol), were added to the white suspension. After other 4 h, N, N'- Carbonyldiimidazole (1.321 g, 8.15 mmol) of another batch was added to the suspension. The reaction was left overnight at rt. The solution was then concentrated in vacuo and methanol was added. The solution was stirred at reflux for 2 h. Then the mixture was evaporated in vacuo, the residue was dissolved in DCM and washed with NaHCC>3 sat. sol. and then with H2O. Organic phase was dried with Na2SO4 anhydrous, filtered and evaporated in vacuo to obtain 550 mg of the title compound, which was used in the following step whitout further purification. MS (ES) {mlz): 199.2 [M+H]+.To a suspension of Sodium hydride (120 mg, 3.00 mmol) in THF (15 mL) activated molecular sieves (0.3 nm, beads about 2 mm) were added. Then, N- hydroxyethanimidamide (commercially available from ABCR, 222 mg, 3.00 mmol) dissolved in THF (8 mL) was added.After 15 min. Methyl 2, 4-bis(methyloxy)-5-pyrimidinecarboxylate (Prep32, 540 mg, 2.72 mmol) dissolved in THF (12 mL) was added. After 10 min. N, N-Dimethylformamide (DMF) (7.00 mL) was added and the reaction mixture was stirred at 60 0C for 4 h. The reaction mixture was filtered and concentrated under reduced pressure to obtain a red oil (195mg).The residue was dissolved in HCI 4M in dioxane (15mL, psiOmmol) and heated at 9OC for2h. Solvents were evaporated under vaccum to obtain 170mg of the title compound as brown solid. MS (ES) (mlz): 196.12 [M+H]+.

Molecular Weight:198.18
XLogP3:0.7
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:198.06405680
Monoisotopic Mass:198.06405680
Topological Polar Surface Area:70.5
Heavy Atom Count:14
Complexity:200
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes