Ethanol → 2,5-Diamino-4,6-dichloropyrimidine

N-(2-Amino-4,6-dichloro 5-pyrimidinyl)formamide (Example 3, 500 mg, 2.42 mmol) was dissolved in 0.1 N hydrochloric acid (5 mL, 2.5 mequiv) and ethanol (7 mL) at reflux. The solution was refluxed for 5 hours. Volatiles were removed in vacuo. The residue was partitioned between water (30 mL) adjusted to pH 8 with dilute ammonium hydroxide and ethyl acetate (75 mL). The ethyl acetate layer was dried (sodium sulfate). Evaporation of the ethyl acetate left pink solid (0.40 g). Recrystallization of the solid from 95% ethanol gave the title compound (IV) as light pink needles (280 mg, 65%); darkens and shrinks to black solid above 85° C., does not become fluid below 300° C.; 1H-NMR (DMSO-d6) and mass spectra identical to those described in Example 4.

1. temperatureThe solution was refluxed for 5 hours
2. customVolatiles were removed in vacuo
3. customThe residue was partitioned between water (30 mL)
4. dry with materialThe ethyl acetate layer was dried (sodium sulfate)
5. customEvaporation of the ethyl acetate
6. waitleft pink solid (0.40 g)
7. customRecrystallization of the solid from 95% ethanol

ORD record

ord-7806f67a6d2e4abcab60acf71cf24c6e

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06448403B1