Nakazawa, Junichi; Watatani, Mitsuo published the artcile< Pyrimidine derivatives. I. Sulfanilamide derivatives>, Product Details of C5H6ClN3O, the main research area is .
4-Sulfanilamido-2,6-disubstituted pyrimidines were prepared A mixture of 3.8 g. 2,6-dihydroxypyrimidine, 38 cc. POCl3, and 9 g. PhNMe2 was refluxed 2 hrs., excess of POCl3 removed, the residue decomposed with ice, the mixture adjusted to pH 2.8, and kept overnight to give 3.9 g. 2,6-dichloro-4-aminopyrimidine (I), needles, m. 270-1° (MeOH). A mixture of 16.3 g. 2-methoxy-4-amino-6-hydroxypyrimidine, 23.6 g. Ac2O, and 23.6 g. AcOH was refluxed 1 hr. to give 19.3 g. 2-methoxy-4-acetamido-6-hydroxypyrimidine (II), m. 275-80° (decomposition). Similarly was prepared 2-ethoxy-4-acetamido-6-hydroxypyrimidine (needles, m. 258-9° (decomposition) (EtOH)). A mixture of II (9 g.) 30.2 POCl3, and 6 g. PhNMe2 was refluxed 1.5 hrs., the excess of POCl3 removed, and the residue decomposed with ice to give 8.6 g. 2-methoxy-4-acetamido-6-chloropyrimidine (III), columns, m. 197-8° (AcOEt). Similarly was prepared 2-ethoxy-4-acetamido-6-chloropyrimidine, columns, m. 193° (C6H6 or AcOEt). III (13 g.) was heated 10 min. with 5.2 g. NaOH and 200 cc. 90% MeOH, the whole neutralized, the MeOH removed, H2O added, and the resulting crystals recrystallized from C6H6 to give 9.1 g. 2-methoxy-4-amino-6-chloropyrimidine (IV), needles, m. 128-9°. Similarly was prepared 2-ethoxy-4-amino-6-chloropyrimidine, needles, m. 128-9° (C6H6). I (1.7 g.) was refluxed 4 hrs. with 1.2 g. NaOH and 12 cc. MeOH, the mixture, filtered, the filtrate concentrated, and H2O added to give 1.5 g. 2,6-dimethoxy-4-aminopyrimidine (V), columns, m. 151-2° (C6H6). Refluxing III or IV with NaOH in MeOH also gave V in 90% yield. Similarly were prepared the following 2,6-RR’ derivatives of 4-aminopyrimidines (R, R’, m.p., and % yield given): OEt, OEt, 107-8°, 95.3; SMe, SMe, 122-3°, 91.6; SEt, SEt, 78-80°, 84; OEt, OMe, 107-8.5°, -; OPh, OMe, 137-8°, 59.9; SMe, OMe, 94-5°, 54.5; SEt, OMe, 78-80°, 52.1; OMe, OEt, 142-3°, 87.6; OEt, SEt, (b1.5 165-9°), 87.3; SPh, OEt, 108.5-9.5°, 70.2. A solution of 4.4 g. V and 7.3 g. 4-acetylsulfanilyl chloride in 14.6 g. C5H5N was kept at room temperature overnight, heated 1 hr. on a steam bath with 73 cc. 10% NaOH solution, H2O added and the mixture evaporated in vacuo, the residue adjusted to pH 4 with HCl, and the resulting crystals recrystallized from MeOH to give 7.8 g. 4-sulfanilamido-2,6-dimethoxypyrimidine, columns, m. 201-2°. Similarly were prepared the following N:C(R).N:C(R’).CH:CNHSO2C6H4NH2-p (data as before): OEt, OEt, 195-6°, 77.8; SMe, SMe, 178-9°, 74.1; SEt, SEt, 178-9°, 79.7; OMe, OEt, -, -; OMe, OPh, 108-10°, 51.4; OMe, SMe, 172-3°, 71.6; OMe, SEt, 175-6°, 73.0; OEt, OMe, 185-6°, 77.9; SEt, OEt, 177-8°, 46.2; OEt, SPh, 206-8°, 61.5.
Takamine Kenkyusho Nenpo published new progress about Alcoholysis. 3286-55-3 belongs to class pyrimidines, and the molecular formula is C5H6ClN3O, Product Details of C5H6ClN3O.
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia