تفاعل #420106

معادلة التفاعل

DMSO

dimethyl sulfoxide

ammonia

methyl 2,6-dichloro-5-methoxy-pyrimidine-4-carboxylate

→

title compound

المردود 50.0%

methyl 6-amino-2-chloro-5-methoxy-pyrimidine-4-carboxylate

المردود 50.0%

المذيبات

ethyl acetate

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىwas prepared
2. 2
   workup.ADDITIONTo this solution was added, at 0-5° C.
3. 3
   ترشيحthe resulting solid was filtered
4. 4
   غسيلThe filtrate was washed with a brine solution
5. 5
   تجفيفThe organic layer was dried over sodium sulfate
6. 6
   تركيزUpon concentration
7. 7
   أخرىthe crude product was obtained
8. 8
   ترشيحfiltered
9. 9
   أخرىto obtain the pure compound
10. 10
    تركيزThe resulting filtrate, after concentration
11. 11
    أخرىpurified

الإجراء التجريبي

A solution comprising the reaction mixture prepared by Example 8, which reaction mixture contained the methyl 2,6-dichloro-5-methoxy-pyrimidine-4-carboxylate (25 g, 0.1 mol), and dimethyl sulfoxide (DMSO) was prepared. To this solution was added, at 0-5° C., a solution of ammonia in DMSO (2 eq). This mixture was stirred at the same 0-5° C. temperature for 10 to 15 minutes. Later, the mixture was diluted with ethyl acetate, and the resulting solid was filtered. The filtrate was washed with a brine solution. The organic layer was dried over sodium sulfate. Upon concentration, the crude product was obtained. The crude product was stirred in a minimum amount of ethyl acetate and filtered to obtain the pure compound. The resulting filtrate, after concentration, was column purified. This produced the title compound (11 g, 50% yield): mp 158° C.; 1H NMR (DMSO-d6) δ 3.71 (s, 3H), 3.86 (s, 3H), 7.65 (brs, 1H), 8.01 (brs, 1H).

المصدر