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CAS No. : | 1820-81-1 | MDL No. : | MFCD00006019 |
Formula : | C4H3ClN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZFTBZKVVGZNMJR-UHFFFAOYSA-N |
M.W : | 146.53 | Pubchem ID : | 15758 |
Synonyms : |
Fluorouracil impurity
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 32.69 |
TPSA : | 65.72 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.44 cm/s |
Log Po/w (iLOGP) : | 0.6 |
Log Po/w (XLOGP3) : | -0.35 |
Log Po/w (WLOGP) : | -0.28 |
Log Po/w (MLOGP) : | -0.53 |
Log Po/w (SILICOS-IT) : | 2.0 |
Consensus Log Po/w : | 0.29 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.02 |
Solubility : | 14.0 mg/ml ; 0.0952 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.57 |
Solubility : | 39.6 mg/ml ; 0.27 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.06 |
Solubility : | 1.27 mg/ml ; 0.00869 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.52 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Neat (no solvent); Heating / reflux | 5-Chlorouracil (4.5 g, 30.82 mmol) was dissolved in phosphorus oxychloride (100 mL) and phosphorus pentachloride (19.2 g, 92.46 mmol) was added. The reaction mixture was heated at reflux overnight; it was then cooled to RT and the solvent was evaporated under reduced pressure. The residue was cooled to 0 0C and ice flakes were carefully added. The resulting mixture was stirred for 10 minutes; it was then partitioned between water and DCM. The organic phase was separated and washed 3 times with water. The aqueous layers were combined and extracted twice with DCM. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure to give f> o fQSpercent vipid) of 2,4, 5-trichloro-pyrimidine as a yellow oil without further purifications. |
81% | at 110℃; for 24 h; | Example 15 N4-[(trans-4-aminocyclohexyl)methyl]-5-chloro-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine To a suspension of 5-chlorouracil (15.0 g, 102.4 mmol) in POCl3 (50 mL, 326.1 mmol) was added N,N-diethylaniline (7.5 mL). The reaction mixture was heated at 110° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated in vacuo to about 25 mL. The resulting residue was then poured into ice and stirred until all the ice melted. The aqueous layer was extracted with ether (*3). The combined organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was distilled under vacuum at ~90° C. to afford 12.5 g (81percent) of 5-chloro-2,4-dichloropyrimidine. |
69% | at 110℃; for 3 h; | Example 1; compound 1 <n="45"/>A 50OmL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 1100C and stirred for 3 h. The reaction was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield crude yellow oil. The crude oil was purified by silica gel chromatography, 0-10percent EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69percent).; Example 3; compound 78NMM, THF -780CA 500-mL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 110 0C and stirred for 3 h. The reaction was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield crude yellow oil. The crude oil was <n="49"/>purified by silica gel chromatography, 0-10percent EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69percent).; Example 4 compound 80A 500-mL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 110 0C and stirred for 3 h. The reaction was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield crude yellow oil. The crude oil was purified by silica gel chromatography, 0-10percent EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69percent).; Example 5 compound 84a bA 50OmL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 1100C and stirred for 3 h. The reaction was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield crude yellow oil. The crude oil was purified by silica gel chromatography, 0-10percent EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69percent). |
69% | at 110℃; for 3.01667 h; | Example 10 N-(2-(2,5 -dichloropyrimidin-4-ylamino)phenyl)-cyclopropanecarboxamide; A 500 mL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 110 0C and stirred for 3 h. The reaction <n="41"/>was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield crude yellow oil. The crude oil was purified by silica gel chromatography, 0-10percent EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69percent).; A 500 mL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 110 0C and stirred for 3 h. The reaction was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield <n="43"/>crude yellow oil. The crude oil was purified by silica gel chromatography, 0-10percent EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69percent). |
51% | With phosphorus pentachloride In water; ethyl acetate; trichlorophosphate | Method 19 2,4,5-Trichloropyrimidine 5-Chlorouracil (10.0 g, 68.5 mmol) was dissolved in phosphorus oxychloride (60 ml) and phosphorus pentachloride (16.0 g, 77 mmol) was added. The reaction mixture was then stirred at reflux (110° C.) for 16 hrs then allowed to cool to 20° C. The reaction mixture was then poured slowly and carefully into water (200 ml) at 25° C. with vigorous stirring. Then stirred well for 90 minutes before addition of EtOAc (250 ml). Organic layer separated off and aqueous layer re-extracted into EtOAc (250 ml). The organic layers were then combined and washed with sodium bicarbonate (200 ml aqueous solution), brine (200 ml) and then evaporated to a yellow liquid. The crude material was purified by column chromatography eluding with dichloromethane to afford the product as a yellow liquid (6.37 g, 51percent). NMR (CDCl3): 8.62 (s, 1H); MS (M+): 182, 184,186. |
51% | With phosphorus pentachloride In ethyl acetate; trichlorophosphate | Method 3 2,4,5-Trichloropyrimidine 5-Chlorouracil (10.0 g, 68.5 mmol) was dissolved in phosphorus oxychloride (60 ml) and phosphorus pentachloride (16.0 g, 77.0 mmol) was added. The mixture was heated under reflux for 16 hours, left to cool and then poured slowly into water (200 ml) with vigorous stirring. The mixture was stiffed for 1.5 hours and then ethyl acetate (250 ml) was added. The organic layer was separated and the aqueous layer was extracted with a further portion of ethyl acetate (250 ml). The combined extracts were washed with saturated sodium bicarbonate (200 ml) and saturated sodium chloride solution (200 ml), and then dried. Volatile material was removed by evaporation and the residue was purified by column chromatography, eluding with DCM, to give the product as a yellow liquid (6.37 g, 51percent). NMR (CDCl3): 8.62 (s, 1H); MS (MH+): 182, 184, 186. |
51% | With phosphorus pentachloride In ethyl acetate; trichlorophosphate | Method 5 2,4,5-Trichloropyrimidine 5-Chlorouracil (10.0 g, 68.5 mmol) was dissolved in phosphorus oxychloride (60 ml) and phosphorus pentachloride (16.0 g, 77.0 mmol) was added. The mixture was heated under reflux for 16 hours, left to cool and then poured slowly into water (200 ml) with vigorous stirring. The mixture was stirred for 1.5 hours and then ethyl acetate (250 ml) was added. The organic layer was separated and the aqueous layer was extracted with a further portion of ethyl acetate (250 ml). The combined extracts were washed with saturated sodium bicarbonate (200 ml) and saturated sodium chloride solution (200 ml), and then dried. Volatile material was removed by evaporation and the residue was purified by column chromatography, eluding with DCM, to give the product as a yellow liquid (6.37 g, 51percent). NMR (CDCl3): 8.62 (s, 1H); MS (MH+): 182, 184, 186. |
51% | With phosphorus pentachloride In ethyl acetate; trichlorophosphate | Method 8 2,4,5-Trichloropyrimidine 5-Chlorouracil (10.0 g, 68.5 mmol) was dissolved in phosphorus oxychloride (60 ml) and phosphorus pentachloride (16.0 g, 77.0 mmol) was added. The mixture was heated under reflux for 16 hours, left to cool and then poured slowly into water (200 ml) with vigorous stirring. The mixture was stirred for 1.5 hours and then ethyl acetate (250 ml) was added. The organic layer was separated and the aqueous layer was extracted with a further portion of ethyl acetate (250 ml). The combined extracts were washed with saturated sodium bicarbonate (200 ml) and saturated sodium chloride (200 ml), and then dried. Volatile material was removed by evaporation and the residue was purified by column chromatography, eluding with DCM, to give the product as a yellow liquid (6.37 g, 51percent). NMR (CDCl3): 8.62 (s, 1H); MS (MH+): 182, 184, 186. |
51% | With phosphorus pentachloride In ethyl acetate; trichlorophosphate | Method 11 2,4,5-Trichloropyrimidine 5-Chlorouracil (10.0 g, 68.5 mmol) was dissolved in phosphorus oxychloride (60 ml) and phosphorus pentachloride (16.0 g, 77.0 mmol) was added. The mixture was heated under reflux for 16 hours, left to cool and then poured slowly into water (200 ml) with vigorous stirring. The mixture was stirred for 1.5 hours and then ethyl acetate (250 ml) was added. The organic layer was separated and the aqueous layer was extracted with a further portion of ethyl acetate (250 ml). The combined extracts were washed with saturated sodium bicarbonate (200 ml) and saturated sodium chloride solution (200 ml), and then dried. Volatile material was removed by evaporation and the residue was purified by column chromatography, eluding with DCM, to give the product as a yellow liquid (6.37 g, 51percent). NMR (CDCl3): 8.62 (s, 1H); MS (MH+): 182, 184, 186. |
82.9% | With N,N-diethylaniline In diethyl ether; trichlorophosphate | 3A Preparation of 2,4,5-trichloropyrimidine 10 g (0.068 mol) of 5-chlorouracil in 20 mL POCl3 (0.21 mol) was treated with 18 mL of N,N-diethylaniline (0.14 mol) at ambient temperature. The stirred mixture was heated to 100° C. for 4 h. Volatile solvents were removed in vacuo and the residue dissolved in 100 mL of diethyl ether and washed with 2*100 mL of ice cold 10percent HCl solution, dried, filtered and evaporated to yield 8.54 g (82.9percent) of 2,4,5-trichloropyrimidine as a colorless liquid. b.p. 73-75° C./3 Torr). |
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