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CAS No. : | 65-86-1 | MDL No. : | MFCD00006027 |
Formula : | C5H4N2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PXQPEWDEAKTCGB-UHFFFAOYSA-N |
M.W : | 156.10 | Pubchem ID : | 967 |
Synonyms : |
6-Carboxyuracil;Vitamin B13
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 34.64 |
TPSA : | 103.02 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) : | -7.84 cm/s |
Log Po/w (iLOGP) : | 0.08 |
Log Po/w (XLOGP3) : | -0.83 |
Log Po/w (WLOGP) : | -1.24 |
Log Po/w (MLOGP) : | -1.04 |
Log Po/w (SILICOS-IT) : | 0.65 |
Consensus Log Po/w : | -0.47 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.62 |
Solubility : | 37.2 mg/ml ; 0.238 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.85 |
Solubility : | 21.9 mg/ml ; 0.14 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.83 |
Solubility : | 23.3 mg/ml ; 0.149 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.85 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319 | 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 |
---|---|---|
92.9% | at 0 - 5℃; for 6 h; Reflux | In a 500 mL three-necked flask,Add orotic acid(15.6 g, 0.10 mol),Then 300 mL of anhydrous methanol was added,Stirring down to 0 ,Maintain the temperature 0 ~ 5 drop add thionyl chloride(10.9 mL, 0.15 mol),And the temperature was raised to reflux for 6 hours.Slightly cold,Vacuum drying solvent,Add 50 mL of anhydrous methanol to lift off.150 mL of methyl t-butyl ether was added,Stirred at room temperature for 1 hour,Filter,Methyl tert-butyl ether wash.dry,To obtain 15.8 g of compound 1,Yield 92.9percent. |
91 g | for 30 h; Reflux | At room temperature, 78 g (0.5 mol) of orotic acid B0 (containing crystal water) and 5 ml of 98percent sulfuric acid were added to 200 ml of methanol and200 ml of dimethyl carbonate solution, refluxed for 30 h, tested with TLC until the reaction was complete, the resulting solid was concentrated, washed with heat Water washed, filtered by water, and then 300ml methanol recrystallization, hot air drying, get white solid, measured melting point: mp: 246 ° C to give 83 g (0.49 mol) of the whey acid ester (B1) in a molar yield of 98percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With trichlorophosphate In N,N-dimethyl-formamide at 110℃; | EXAMPLE 2 Preparation of (S)-6-(( 1 -amino- l-oxopropan-2-yl)amino)-2-(4-(4- fluorophenoxy) phenyl)pyrimidine-4-carboxamide (Cpd No. 1) Scheme 2 2,6-dichloropyrimidine-4-carbonyl chloride: A mixture of orotic acid mono hydrate (34.828 g, 200.0 mmol), phosphorus oxychloride (100 mL, 1092 mmol) and 20 drops of DMF were heated at 1 10°C overnight. After cooling, the dark mixture was diluted with 500 mL hexanes and vigorously stirred. The hexane layer was decanted and quickly washed with water (1 x 100 mL) then brine (1 x 100 mL) and dried over MgS04. The organics were filtered and carefully evaporated in vacuo to give 2,6-dichloropyrimidine-4-carbonyl chloride as a light yellow liquid (26.13 g, 123.6 mmol, 62percent yield). Ή NMR (400 MHz, CDC13): 7.93 (1 H, s). |
62% | at 110℃; | A mixture of orotic acid mono hydrate (34.828 g, 200.0 mmol), phosphorus oxychloride ( 100 mL, 1092 mmol) and 20 drops of DMF were heated at 1 10°C overnight. After cooling, the dark mixture was treated with 500 mL hexanes and vigorously stirred. The hexane layer was decanted and quickly washed with water ( 1 x 100 mL) and brine ( 1 x 100 mL) and dried over MgS04. The organics were filtered and carefully evaporated in vacuo to give 2,6-dichloropyrimidine-4-carbonyl chloride as a light yellow liquid (26.13 g, 123.6 mmol, 62percent yield). ? NMR (400 MHz, CDC13): 7.93 ( 1 H, s). |
62% | at 110℃; | A mixture of orotic acid mono hydrate (34.828 g, 200.0 mmol), phosphorus oxychlride (100 mL, 1092 mmol) and 20 drops of DMF were heated at 110°C overnight. After cooling, the dark mixture was diluted with 500 mL hexanes and vigorously stirred. The hexane layer was decanted and quickly washed with water (1 x 100 mL) then brine (1 x 100 mL) and dried over MgSO4. The organics were filtered and carefully evaporated in vacuo to give 2,6-dichloropyrimidine-4-carbonyl chloride as a light yellow liquid (26.13 g, 123.6 mmol, 62percent yield). 1H NMR (400 MHz, CDCl3): 7.93 (1 H, s). |
62% | With trichlorophosphate In N,N-dimethyl-formamide at 110℃; | EXAMPLE 1 Synthesis of 2,6-dichloropyrimidine-4-carboxamide (Compound 3) A mixture of orotic acid mono hydrate (Compound 1) (34.828 g, 0.200 mol, Aldrich), phosphorus oxychloride (100 mL, 1.092 mol) and 20 drops of DMF were heated at 110°C overnight. After cooling the dark mixture was diluted with 500 mL hexanes and vigorously stirred. The hexane layer was decanted and quickly washed with water (1 x 100 mL) and brine (1 x 100 mL), and dried over MgSO4. The organics were filtered and carefully evaporated in vacuo to give Compound 2 as a light yellow liquid (26.13 g). Yield: 62percent. 1H NMR (400 MHz, CDCl3): δ 7.93 (s, 1 H). |
62% | at 110℃; | A mixture of Compound 3 (34.828 g, 0.200 mol) (Aldrich), phosphorus oxychloride (100 mL, 1.092 mol) and 20 drops of DMF were heated at 110° C. overnight. After cooling the dark mixture was diluted with hexanes (500 mL) and vigorously stirred. The hexane layer was decanted, quickly washed with water (100 mL), brine (100 mL) and dried over MgSO4. The organic layer was filtered and carefully evaporated in vacuo to give 26.13 g (62percent) of Compound 4 as a light yellow liquid. 1H NMR (400 MHz, CDCl3): δ 7.93 (s, 1H). |
62% | With trichlorophosphate In N,N-dimethyl-formamide at 110℃; | A mixture of Compound 14 (34.83 g, 0.200 mol) (Aldrich), phosphorus oxychioride (100 mL, 1.092 mol) and 20 drops of DMF were heated at 110 °C overnight. After coolingthe dark mixture was diluted with hexanes (500 mL) and vigorously stuffed. The hexanelayer was decanted, quickly washed with water (100 mL), brine (100 mL) and dried overMg504. The organic layer was filtered and carefully evaporated in vacuo to give 26.13 g(62percent) of Compound 15 as a light yellow liquid. 1H NMR (400 MHz, CDC13): ö 7.93 (s, 1H). |
62% | at 110℃; | EXAMPLE 1 Synthesis of (S)-6-((l-amino-l-oxopropan-2-yl)amino)-2-chloropyrimidine-4-carboxamide (Compound 5) 5 A mixture of Compound 1 (34.828 g, 0.200 mol) (Aldrich), phosphorus oxychloride (100 mL, 1.092 mol) and 20 drops of DMF were heated at 110 °C overnight. After cooling the dark mixture was diluted with hexanes (500 mL) and vigorously stirred. The hexane layer was decanted, quickly washed with water (100 mL), brine (100 mL) and dried over MgS04. The organic layer was filtered and carefully evaporated in vacuo to give 26.13 g (62percent) of Compound 2 as a light yellow liquid. ]H NMR (400 MHz, CDC13): δ 7.93 (s, 1 H). |
62% | at 110℃; | A mixture of Compound 1 (34.828 g, 0.200 mol, Sigma-Aldrich), phosphorus oxychioride (100 mL, 1.092 mol) and 20 drops of DMF were heated at 110 °C overnight. After cooling to RT the dark mixture was diluted with hexanes (500 mL) and vigorouslystirred. The hexane layer was decanted, quickly washed with water (100 mL), brine (100 mL) and dried over Mg504. The organic layer was filtered and carefully evaporated in vacuo to give Compound 2 as a light yellow liquid (26.13 g). Yield 62percent1H NMR (400 MHz, CDC13): ö 7.93 (s, 1 H). |
62% | at 110℃; | A mixture of Compound 1 (34.8 g, 0.20 mol, Aldrich), phosphorus oxychloride (100 mL, 1.09 mol) and 20 drops of DMF were heated at 110° C. overnight. After cooling to RT the dark mixture was diluted with hexanes (500 mL) and vigorously stirred. The hexane layer was decanted, quickly washed with water (100 mL), brine (100 mL) and dried over MgSO4. The organic layer was filtered and carefully evaporated in vacuo to give Compound 2 as a light yellow liquid (26.13 g). Yield 62percent. 1H NMR (400 MHz, CDCl3): δ 7.93 (s, 1H). |
62% | With trichlorophosphate In N,N-dimethyl-formamide at 110℃; | A mixture of Compound 1 (34.828 g, 0.200 mol) (Aldrich), phosphorus oxychloride (100 mE, 1.092 mol) and 20 drops of DMF were heated at 1100 C. overnight. After cooling the dark mixture was diluted with hexanes (500 mE) and vigorously stirred. The hexane layer was decanted, quickly washed with water (100 mE), brine (100 mE) and dried over MgSO4. The organic layer was filtered and carefully evaporated in vacuo to give 26.13 g (62percent) of Compound 2 as a light yellow liquid. ‘H NMR (400 MHz, CDC13): ö 7.93 (s, 1H). |
62% | at 110℃; | A mixture of 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid (Compound 146, 34.8 g, 0.20 mol, Aldrich), phosphorus oxychloride (100 mL, 1.09 mol) and 20 drops of DMF were heated at 110° C. overnight. After cooling to RT the dark mixture was diluted with hexanes (500 mL) and vigorously stirred. The hexane layer was decanted, quickly washed with water (100 mL), brine (100 mL) and dried over MgSO4. The organic layer was filtered and carefully evaporated in vacuo to give 2,6-dichloropyrimidine-4-carbonyl chloride (Compound 147) as a light yellow liquid (26.13 g). Yield 62percent. 1H NMR (400 MHz, CDCl3): δ7.93 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | Reflux | To a stirred POCl3 (CAUTION—toxic) (30 mL) was added in portions 2,6-dihydroxypyrimidine-4-carboxylic acid (6.0 g,38.5 mmol, CAS 65-86-1) at room temperature. After the addition, PCl5 (CAUTION—toxic) (26.4 mg, 0.127 mmol) was added in portions to the mixture at room temperature. After this addition, the reaction mixture was heated to reflux and stirred at reflux overnight.TLC indicated that the reaction was complete. Most of the excess POCl3 was removed by distillation, and the residue was distilled under reduced pressure to give compound 9 (bp: 158–160 C 1 mm/Hg pressure, 5 g, 44percent) as a yellow oil. |
22% | at 20℃; for 3 h; Reflux | Step 2: 2,6-dichloro-pyrimidine-4-carboxylic acid chloride 20 g (0.13 mol) 2,6-dihydroxy-pyrimidine-4-carboxylic acid were refluxed together with 40 mL phosphorus oxychloride. After cooling to RT 60 g (0.29 mol) phosphorus-(V)-chloride were added and refluxing was continued for a further 3 h. The product was obtained by fractional distillation. Yield: 6.00 g (22percent of theoretical) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19 g | Stage #1: With trichlorophosphate In N,N-dimethyl-formamide for 3 h; Reflux Stage #2: at 0℃; |
To a stirred suspension of orotic acid (CAS Number 65-86-1 , available from Alfa Aesar) (20.00 g, 128.140 mmol) in POCI3(75 ml) was added DMF (catalytic amount, -0.5 ml) at ambient temperature and the resulting reaction mixture was refluxed for 3 h. Excess of POC was removed by vacuum distillation after 3h of reflux. The obtained slurry was poured slowly in 5percent mixture of methanol in chloroform (200 ml) at 0°C and stirred for 30 min. The organic layer obtained was washed with saturated solution of NaHCC>3 (3 x 200 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure yielding methyl 2,6-dichloropyrimidine-4-carboxylate (19.00 g, 91 .800 mmol), which was used in the next step without further purification. |
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