Ammonia → 4-Amino-2-chloro-5-iodo-6-methoxycarbonylpyrimidine

2,6-Dichloro-5-iodopyrimidine-4-carboxylic acid methyl ester (12 g, 36 mmol) was dissolved in dry dimethyl sulfoxide (DMSO; 100 mL) and treated with a stream of ammonia at such a rate when combined with external water bath cooling to keep the temperature in the range of 20-30° C. After 90 min, the ammonia addition was complete and excess ammonia was removed from the mixture by sparging with a stream of nitrogen for 20 min. The mixture was poured into water (200 mL) with stirring and the precipitated product was extracted with ethyl acetate (75 mL) twice. The combined ethyl acetate extracts were washed twice with water (50 mL), once with saturated NaCl solution, dried and evaporated to give the title compound (10 g, 89% yield) that was used without further purification. MS: M/Z=313.

1. customcombined with external water bath
2. temperaturecooling
3. customin the range of 20-30° C
4. customexcess ammonia was removed from the mixture
5. customby sparging with a stream of nitrogen for 20 min
6. additionThe mixture was poured into water (200 mL)
7. extractionthe precipitated product was extracted with ethyl acetate (75 mL) twice
8. washThe combined ethyl acetate extracts were washed twice with water (50 mL), once with saturated NaCl solution
9. customdried
10. customevaporated

ORD record

ord-97b0ce57df6a4b04b2a35ddc1e4b782d

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268753B2