*Storage: Inert atmosphere,Room Temperature.
*Shipping: Normal
4.5
*For Research Use Only !
Change View
Size | Price | USA Stock *0-1 Day | Global Stock *5-7 Days | In Stock |
250mg | łÇǶÊÊ | Inquiry | Inquiry | Login |
1g | łËʶÊÊ | Inquiry | Inquiry | Login |
5g | łÍͶÊÊ | Inquiry | Inquiry | Login |
10g | łó˶ÊÊ | In Stock | In Stock | Login |
25g | łÇďò¶ÊÊ | In Stock | In Stock | Login |
Please Login or Create an Account to: See VIP prices and availability
łÇǶÊÊ
łËʶÊÊ
łÍͶÊÊ
łó˶ÊÊ
łÇďò¶ÊÊ
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 37554-70-4 |
Formula : | C5H4ClFN2O |
M.W : | 162.55 |
SMILES Code : | COC1=NC(Cl)=NC=C1F |
MDL No. : | MFCD07440062 |
Boiling Point : | No data available |
InChI Key : | HLVJKADQILYNGE-UHFFFAOYSA-N |
Pubchem ID : | 13530704 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 33.49 |
TPSA ? Topological Polar Surface Area: Calculated from | 35.01 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 2.02 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 1.57 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 1.7 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 0.78 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 2.0 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.61 |
Log S (ESOL):? ESOL: Topological method implemented from | -2.21 |
Solubility | 0.991 mg/ml ; 0.0061 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -1.92 |
Solubility | 1.97 mg/ml ; 0.0121 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -2.67 |
Solubility | 0.352 mg/ml ; 0.00216 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -6.18 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 1.84 |
* 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 |
---|---|---|
75% | In methanol; at 0 - 20℃; for 12.0h; | 2-Chloro-5-fluoro-4-methoxypyrimidine; To a stirred solution of 2,4-dichloro-5-fluoropyrimidine (30.0 g, 180.7 mmol) in MeOH (200 ml) cooled to 0 C was slowly added NaOMe (19.5 g, 361.4 mmol). The mixture was stirred at room temperature for 12 h. At the end of the reaction, the solvent was removed by evaporation. The residue was partitioned between CH2Cl2 (200 ml) and H2O (200 ml). The CH2Cl2 layer was washed with brine (200 ml), dried over Na2SO4 and concentrated in vacuo to give 22.0 g (75% yield) of the product as a white solid. |
7.38% | In tetrahydrofuran; at -10 - 20℃; | Preparation of compound 55a: 2-chloro-5-fluoro-4-methoxypyrimidine2,4-Dichloro-5-fluoropyrimidine (515 mg, 3.08 mmol) was weighed into a 150 mL RBF, and was suspended in THF (5.0 mL). The stirring suspension was cooled to -10 C. NaOMe (250 mg, 4.63 mmol) was added in one portion at -10 C. An additional 0.5 eq of NaOMe were added and the suspension was stirred at RT for 21 h. The suspension was diluted with MeOH, and the the solvents were removed in vacuo. The crude material was purified by flash chromatography (eluting with 100%o DCM) to give 2-chloro-5- fluoro-4-methoxypyrimidine (37 mg, 0.228 mmol, 7.38 %> ) as an amorphous white solid. MS (ESI, pos. ion) m/z: 162.9 (M+l). .H NMR (400 MHz, DMSO-d6) delta ppm 8.60 (d, J=2.7 Hz, 1 H), 4.04 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sodium; at 20℃; | Sodium (0.45 g, 19.6 mmol) was added in portions to methanol (20 mL). Once all the sodium had reacted, a solution of 2,4-dichloro-5-fluoropyrimidine (Preparation 15a, 3.25 g, 19.5 mmol) in methanol (10 mL) was added and the mixture was stirred at ambient temperature overnight. The mixture was diluted with water and extracted with diethyl ether. The organic layer was washed with water, brine, dried (MgS04), filtered and the solvent was removed under reduced pressure to give the title compound (81%) as an orange solid, which was used without further purification.LRMS (m/z): 163 (M+1)+.H-NMR 5 (CDCI3): 4.11 (s, 3H), 8.20 (d, 1 H) |
81% | title compound (81%) as an orange solid, which was used without further purification.LRMS (m/z): 163 (M+1)+.1H-NMR delta (CDCl3): 4.11 (s, 3H), 8.20 (d, 1 H) | |
80% | With sodium; at 20℃; | To a mixture of sodium (450 mg, 19 mmol) in methanol (20 mL) was added a solution of 2,4-dichloro-5-fluoropyrimidine (3.25 g, 19 mmol) in methanol (10ml_). The reaction mixture was stirred at room temperature overnight before being partitioned between water and diethyl ether. The organic phase was separated, washed with brine and evaporated to dryness to give the title compound as an orange oil (80%), which was used in the next step without further purification.1H-NMR delta (400 MHz, CDCI3): 4.1 (s, 3H), 8.2 (s, 1 H). |
80% | With sodium; at 20℃; | sodium (450 mg, 19 mmol) in methanol (20 mL) was added a solution of 2,4-dichloro-5-fluoropyrimidine (3.25 g, 19 mmol) in methanol (10mL). The reaction mixture was stirred at room temperature overnight before being partitioned between water and diethyl ether. The organic phase was separated, washed with brine and evaporated to dryness to give the title compound as an orange oil (80%), which was used in the next step without further purification.1H-NMR delta (400 MHz, CDCl3): 4.11 (s, 3H), 8.20 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 80℃; for 12.0h; | General procedure: (5-Fluoro-4-methoxypyrimidin-2-yl)isobutylamine; To a stirred solution of <strong>[37554-70-4]2-chloro-5-fluoro-4-methoxypyrimidine</strong> (10.0 g, 61.7 mmol) and isobutylamine (6.8 g, 92.6 mmol) in MeCN (200 ml) was added DIEA (11.9 g, 92.6 mmol). The mixture was stirred at 80 C for 12 h. At the end of the reaction, the resulting mixture was cooled and partitioned between EtOAc (200 ml) and H2O (200 ml). The EtOAc layer was washed with brine (200 ml), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 2-5% EtOAc/PE to afford 5.2 g (42% yield) of the product as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 80℃; for 12.0h; | General procedure: (5-Fluoro-4-methoxypyrimidin-2-yl)isobutylamine; To a stirred solution of <strong>[37554-70-4]2-chloro-5-fluoro-4-methoxypyrimidine</strong> (10.0 g, 61.7 mmol) and isobutylamine (6.8 g, 92.6 mmol) in MeCN (200 ml) was added DIEA (11.9 g, 92.6 mmol). The mixture was stirred at 80 C for 12 h. At the end of the reaction, the resulting mixture was cooled and partitioned between EtOAc (200 ml) and H2O (200 ml). The EtOAc layer was washed with brine (200 ml), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 2-5% EtOAc/PE to afford 5.2 g (42% yield) of the product as a yellow solid.1H NMR (400 MHz, CDCl3) delta 7.92 (d, J = 2.8 Hz, 1H), 5.03 (br s, 1H), 3.99 (s, 3H), 3.21 (t, J = 6.4 Hz, 2H), 1.91 (m, 1H), 0.99 (d, J = 6.4 Hz, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; for 12.0h;Inert atmosphere; Reflux; | (5-Fluoro-4-methoxypyrimidin-2-yl)phenylamine; To a stirred solution of <strong>[37554-70-4]2-chloro-5-fluoro-4-methoxypyrimidine</strong> (16.0 g, 98.8 mmol) and phenylamine (13.8 g, 141.8 mmol) in 1,4-dioxane (500 ml) was added Cs2CO3 (97.8 g, 296.3 mmol) followed by Pd2(dba)3 (2.7 g, 2.9 mmol) and BINAP (3.1 g, 4.9 mmol) under N2. The mixture was heated at reflux for 12 h. On completion, the mixture was filtered to remove the inorganic salts and the filtrate was partitioned between CH2Cl2 (500 ml) and H2O (500 ml). The CH2Cl2 layer was washed with brine (500 ml), dried over NaSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 5% EtOAc/PE, to afford 13.0 g (63% yield) of the product as a yellow solid.1H NMR (400 MHz, CDCl3) delta 8.07 (d, J = 2.8 Hz, 1H), 7.61 (d, J = 8.0 Hz, 2H), 7.34 (m, 2H), 7.16 (br s, 1H), 7.07 (m, 1H), 4.06 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With caesium carbonate; XPhos;palladium diacetate; at 120℃; for 16.0h;Sealed tube; Inert atmosphere; | Palladium (II) acetate (2.79 mg, 0.012 mmol) was added to a stirred suspension of 2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[l,5-a]pyrazin-4-one (100 mg, 0.41 mmol), cesium carbonate (0.18 g, 0.57 mmol), 2-dicyclohexylphosphino-2',4',6'- triisopropylbiphenyl (17 mg, 0.037 mmol) and <strong>[37554-70-4]2-chloro-5-fluoro-4-methoxypyrimidine</strong> (0.2 g, 1.23 mmol) in a sealed tube and under nitrogen. The reaction mixture was stirred at 120 C for 16 hours. The solvent was evaporated in vacuo and the crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo to yield 5-(5-fluoro-4-methoxy- pyrimidin-2-yl)-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[ 1 ,5-a]pyrazin-4-one (50 mg, 33% yield) as a white solid. 1H NMR (500 MHz, CDC13) delta ppm 4.10 (s, 3 H), 4.41 - 4.57 (m, 4 H), 5.12 (s, 2 H), 6.93 - 7.04 (m, 3 H), 7.09 (s, 1 H), 7.27 - 7.34 (m, 2 H), 8.28 (d, J=2.3 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.7% | With potassium phosphate; XPhos;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; water; at 130℃; for 0.333333h;microwave irradiation; Inert atmosphere; Sealed tube; | Preparation of compound 55b: N-tert-butyl-5-(3-(5-fluoro-4-methoxypyrimidin-2- yl)-l-tosyl-lH-indol-5-yl)-l,3,4-oxadiazol-2-amine N-tert-Butyl-5-(3-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-y^^l,3,4-oxadiazol-2-amine (166 mg, 0.309 mmol), dicyclohexyl(2',4',6'- triisopropylbiphenyl-2-yl)phosphine (6.63 mg, 0.014 mmol) (Strem), Pd2(dba)3 (6.37 mg, 6.96 muiotaetaomicron) (Strem), potassium phosphate (148 mg, 0.696 mmol) (Sigma-Aldrich) and 2- chloro-5-fluoro-4-methoxypyrimidine (37.7 mg, 0.232 mmol) were weighed into a 5 mL glass microwave tube. The tube was purged with argon and the solids were treated with dioxane (2 mL) and water (0.200 mL). The tube was sealed, and the contents were heated an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 130 C for 20 min. The mixture was treated with H20 and extracted with EtOAc. The organic layer was washed with brine, dried over MgS04, filtered and concentrated. The crude material was purified by flash chromatography (eluting with 5-60% EtOAc in Hex) to give N-tert-butyl-5-(3-(5-fluoro-4-methoxypyrimidin-2-yl)-l-tosyl-lH-indol-5-yl)- l,3,4-oxadiazol-2-amine (75.5 mg, 0.141 mmol, 60.7 % ) as an off white solid. MS (ESI, pos. ion) m/z: 537.0 (M+l). .H NMR (400 MHz, DMSO-d6) delta ppm 8.98 - 9.03 (m, 1 H), 8.72 (d, J=3.1 Hz, 1 H), 8.56 (s, 1 H), 8.16 (d, J=8.8 Hz, 1 H), 8.02 - 8.07 (m, 2 H), 7.86 - 7.92 (m, 1 H), 7.64 (s, 1 H), 7.40 - 7.48 (m, 2 H), 4.22 (s, 3 H), 2.33 (s, 3 H), 1.35 - 1.41 (m, 9 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With potassium phosphate; XPhos;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; water; at 130℃; for 0.5h;microwave irradiation; Inert atmosphere; Sealed tube; | Preparation of compound 56b: N-tert-butyl-5-(3-(4-cyclopropyl-5-fluoropyrimidin- 2-yl)-l-tosyl-lH-indol-5-yl)-l,3,4-oxadiazol-2-amineTo a 5 mL glass microwave tube containing N-tert-butyl-5-(3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-l-tosyl-lH-indol-5-yl)-l,3,4-oxadiazol-2-amine (166 mg, 0.309 mmol) was added 2-chloro-4-cyclopropyl-5-fluoropyrimidine (69.4 mg, 0.402 mmol), potassium phosphate (197 mg, 0.928 mmol), dicyclohexyl(2',4',6'-triisopropylbiphenyl-2- yl)phosphine (8.9 mg, 0.019 mmol), and Pd2(dba)3 (8.5 mg, 9.28 muiotaetaomicron). The tube was purged with argon, the solids were treated with dioxane (3 mL) and Water (0.3 mL), the tube was sealed, and the contents were heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 130 C for 30 min. The mixture was treated with H20 and extracted with EtOAc. The organic layer was washed with brine, dried over MgS04, filtered and concentrated. The crude material was purified by flash chromatography (eluting with 5-60% EtOAc in Hex) affording N-tert-butyl-5-(3-(4- cyclopropyl-5-fluoropyrimidin-2-yl)-l osyl-lH-indol-5-yl)-l,3,4-oxadiazol-2-amine (129 mg, 76 % ) as a light yellow viscous oil. MS (ESI, pos. ion) m/z: 547.1 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanesulfonic acid; In 1,4-dioxane; at 100℃; | INTERMEDIATE 9: 5-fluoro-4-methoxy-N-[3-methyl-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl]pyrimidin-2-amineTo a flask containing <strong>[37554-70-4]2-chloro-5-fluoro-4-methoxypyrimidine</strong> (0.32 g, 1.97 mmol) and 3-methyl- 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (0.40 g, 1.72 mmol) were added dioxane (17 mL) and methanesulfonic acid (0.13 mL, 1.97 mmol). The reaction was heated at 100C overnight. The reaction was then cooled to room temperature, diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. Flash chromatography was used for purification to yield 5-fluoro-4-methoxy-N-[3-methyl-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl]pyrimidin-2-amine. MS ESI calc'd for Ci8H2 BFN303 [M + H]+ 360, found 360. H NMR (500 MHz, DMSO-d6) delta 9.51 (s, 1H), 8.27 (d, J= 3.2, 1H), 8.00 (s, 1H),7.57 (s, 1H), 7.07 (s, 1H), 4.01 (s, 3H), 2.25 (s, 3H), 1.26 (s, 12H). | |
With methanesulfonic acid; In 1,4-dioxane; at 100℃; | Preparative Example 1.3 - 5-Fluoro-4-methoxy-N-[3-methyl-5-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)phenyl]pyrimidin-2-amine PrepEx. 1.3 [00217] A solution of <strong>[37554-70-4]2-chloro-5-fluoro-4-methoxypyrimidine</strong> (0.32 g, 1.97 mmol) and 3- methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (0.40 g, 1.72 mmol) in dioxane (17 mL) and methanesulfonic acid (0.13 mL, 1.97 mmol) was heated to 100C overnight. The reaction was then cooled to room temperature, diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated in reduced pressure. The residue was purified by chromatography on silica gel to afford 5-fluoro-4-methoxy-N-[3-methyl-5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]pyrimidin-2-amine. MS ESI calc'd for Ci8H24BFN303 [M + H]+ 360, found 360. 'H NMR (500 MHz, DMSO-d6) delta 9.51 (s, 1H), 8.27 (d, J= 3.2, 1H), 8.00 (s, 1H), 7.57 (s, 1H), 7.07 (s, 1H), 4.01 (s, 3H), 2.25 (s, 3H), 1.26 (s, 12H). | |
With methanesulfonic acid; In 1,4-dioxane; at 100℃; | Preparative Example 1.11 5-Fluoro-4-methoxy-N-[3-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl]pyrimidin-2-amine Methanesulfonic acid (0.13 mL, 1.97 mmol) was added to a solution of 2-chloro- 5-fluoro-4-methoxypyrimidine (0.32 g, 1.97 mmol) and 3-methyl-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)aniline (0.40 g, 1.72 mmol) in dioxane (17 mL). The reaction mixture was heated at 100C overnight. The reaction was then cooled to room temperature, diluted with EtOAc, washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to afford 5- fluoro-4-methoxy-N-[3-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]- pyrimidin-2-amine. MS ESI calc'd for CisH^BF sOs [M + H]+ 360, found 360. lH NMR (500 MHz, DMSO-d6) delta 9.51 (s, IH), 8.27 (d, J= 3.2, IH), 8.00 (s, IH), 7.57 (s, IH), 7.07 (s, IH), 4.01 (s, 3H), 2.25 (s, 3H), 1.26 (s, 12H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With palladium diacetate; caesium carbonate; XPhos; In 1,4-dioxane; at 100℃; for 18.0h;Sealed tube; Inert atmosphere; | 22. PREPARATION OF 5-(5-FLUORO-4-METHOXY-PYRIMIDIN-2-YL)-2- PHENOXYMETHYL-6,7-DIHYDRO-5H-OXAZOLO[5,4-C] PYRIDIN-4-ONE (EXAMPLE B22). [00522] Palladium (II) acetate (2.78 mg, 0.012 mmol) was added to a stirred suspension of 2-phenoxymethyl-6,7-dihydro-5H-oxazolo[5,4-c]pyridin-4-one (0.1 g, 0.41 mmol), 2-chloro- 5-fluoro-4-methoxy-pyrimidine (0.13 g, 0.82 mmol), cesium carbonate (0.187 g, 0.57 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.018 g, 0.037 mmol) in 1,4- dioxane (2 mL) in a sealed tube and under nitrogen. The mixture was stirred at 100 C for 18 h. The solvents were evaporated in vacuo and the crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 80/20). The desired fractions were collected, the solvents evaporated in vacuo and triturated with diethyl ether to yield the title compound (0.109 g, 72% yield ) as a white solid. d8Hi5FN404. 1H NMR (400 MHz, CDC13) delta ppm 3.07 (t, J= 6.7 Hz, 2 H), 4.08 (s, 3 H), 4.36 (t, J= 6.7 Hz, 2 H), 5.23 (s, 2 H), 6.98 - 7.06 (m, 3 H), 7.28 - 7.36 (m, 2 H), 8.26 (d, J= 2.5 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 90℃; for 48.0h;Inert atmosphere; | A mixture of zinc(II) cyanide (10.8 g, 92 mmol) and <strong>[37554-70-4]2-chloro-5-fluoro-4-methoxypyrimidine</strong> (15.0 g, 92 mmol) in dimethylformamide (200 mL) was degassed at room temperature by bubbling nitrogen through the solution for 10 min. Tetrakis(triphenylphosphine)palladium(0) (10.0 g, 8.65 mmol) was added, degassing was continued another 10 min and the reaction was heated 2 days at 90C. The mixture was cooled to room temperature and diluted with ethyl acetate (150 mL), brine (50 mL) and concentrated aqueous ammonium hydroxide (10 mL). After mixing, the layers were separated and the aqueous phase was extracted with another portion of ethyl acetate (150 mL). The combined organic phases were washed with 2 x 20 mL brine then dried over sodium sulfate, filtered and concentrated by rotary evaporation at 60C. Purification over Si02 with a hexane/ethyl acetate gradient gave recovered chloropyrimidine starting material and 5.5 g of the desired cyano pyrimidine as a colorless oil. The recovered starting material was reprocessed as above to give another 3.0 g of the depicted intermediate (total yield 8.5 g, 60% yield). -NuMuRho (500 MHz, CDC13) delta 8.41 (s, 1H), 4.17 (s, 3H) ppm. |
Tags: 37554-70-4 synthesis path| 37554-70-4 SDS| 37554-70-4 COA| 37554-70-4 purity| 37554-70-4 application| 37554-70-4 NMR| 37554-70-4 COA| 37554-70-4 structure
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :
Total Compounds: mg
The concentration of the dissolution solution you need to prepare is mg/mL