The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of hydroxyamino acids and N-methyl derivatives. III. Synthesis of DL-serine and N-methylserine》. Authors are Izumiya, Nobuo.The article about the compound:2-Bromo-3-methoxypropanoic acidcas:65090-78-0,SMILESS:O=C(O)C(Br)COC).Name: 2-Bromo-3-methoxypropanoic acid. Through the article, more information about this compound (cas:65090-78-0) is conveyed.
cf. C.A. 45, 4656e. Exptl. procedures for the synthesis of DL-serine and N-methylserine from CH2:CHCO2H (I) are described. I (14.4 g.) added to 14 g. Hg(OAc)2 in 300 cc. of MeOH, and gave after 2 days 54 g. α-acetoxymercuri-β-methoxypropionic acid, m. 200-4°; to this in 200 cc. water and 36 g. KBr, in direct sunlight, was added dropwise 32 g. Br and 36 g. KBr in 60 cc. water; extraction of the mixture with ether after addition of 33 cc. 48% HBr gave 37 g. crude α-bromo-β-methoxypropionic acid (II), b4 92-5°. Aqueous NH3 with 37 g. II gave the α-amino acid (III), decompose 233-4°, in 34% yield (based on I); Cu salt, C8H16O6N2Cu, scarcely soluble in water; phenylurea, MeOCH2CH(NHCONHPh)CO2H, m. 171-2°; N-(p-tolylsulfonyl) derivative (IV), m. 139-41°. Serine was obtained by boiling crude III with 48% HBr (yield 41%, based on I). Heating IV with MeI and 2 N NaOH 1 hr. in a sealed tube at 70° gave β-methoxy-α-[methyl(p-tolylsulfonyl)amino]propionic acid (V), C12H17O5NS, m. 92°. Heating crude 3.7 g. II and 35% 9 cc. MeNH2 4 hrs. in a sealed tube at 100° gave 0.74 g. β-methoxy- α-(methylamino)propionic acid (VI), m. 233° (decomposition); picrolonate, C15H19O8N5, m. 120-1° (decomposition); Cu salt, C10H20O6N2Cu.3H2O, m. 234° (decomposition). The crude product from II and MeNH2 gave with 48% HBr N-methylserine, m. 203-4° (decomposition), 30% yield (based on I); picrolonate, C14H17O8N5, m. 130-4° (decomposition); Cu salt, C8H16O6N2Cu, m. 197-8° (decomposition). VI was also obtained by hydrolysis of V with concentrated HCl.
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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia