Carbamimidic acid, methyl ester, sulfate (1:1) → 4-(2-Azido-ethoxymethyl)-6-(2-chloro-phenyl)-2-methoxy-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester

Temperature

80 °C

A mixture of 2-[2-(2-azido-ethoxy)-acetyl]-3-(2-chloro-phenyl)-acrylic acid ethyl ester (1.50 g, 4.44 mmol), O-methylisourea sulfate (0.82 g, 6.66 mmol) and sodium bicarbonate (1.5 g, 17.86 mmol) in N,N-dimethylacetamide (25 mL) was heated to 80° C. and maintained at this temperature overnight (ca. 15 h). The mixture was cooled to RT and then taken up in EtOAc (100 mL) and H2O (50 mL). The EtOAc extract was washed with brine (50 mL), dried (Na2SO4), filtered, concentrated and dried in vacuo. The crude product was purified by chromatography using the ISCO Combiflash SQ16× (120 g Redisep silica gel column, 0 to 60% EtOAc in hexanes for 30 min at 40 mL/min) to afford 1.189 g (68% for 2 steps) of white solid as a purified product.

1. temperaturemaintained at this temperature overnight (ca. 15 h)
2. temperatureThe mixture was cooled to RT
3. extractionThe EtOAc extract
4. washwas washed with brine (50 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customdried in vacuo
9. customThe crude product was purified by chromatography
10. custom× (120 g Redisep silica gel column, 0 to 60% EtOAc in hexanes for 30 min at 40 mL/min) to afford 1.189 g (68% for 2 steps) of white solid as a purified product

ORD record

ord-03754c4907c54f78906b5bdeaf63142d

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07166603B2