Structure of 2164-67-2
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
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. : | 2164-67-2 |
Formula : | C5H7N3O |
M.W : | 125.13 |
SMILES Code : | OCC1=NC(N)=NC=C1 |
MDL No. : | MFCD01689391 |
InChI Key : | TWYCDZQLLFNFGK-UHFFFAOYSA-N |
Pubchem ID : | 200493 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 32.56 |
TPSA ? Topological Polar Surface Area: Calculated from |
72.03 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.82 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-1.0 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.59 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-1.16 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.06 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.38 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.41 |
Solubility | 48.3 mg/ml ; 0.386 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.03 |
Solubility | 118.0 mg/ml ; 0.942 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.08 |
Solubility | 10.4 mg/ml ; 0.0832 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 |
No |
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) |
No |
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 |
-7.77 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) |
1.59 |
* 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 |
---|---|---|
With methanol; sodium tetrahydroborate; at 0 - 20℃; for 2h; | General procedure: To a solution of aldehyde in the indicated solvent is added sodium borohydride at 0 °C. After stirring at room temperature for 2 hours, water is added and the mixture is concentrated.Following Procedure C using crude 4 (1.0 g, 6.35 mmol), MeOH, and sodium borohy dride (360 mg, 9.55 mmol), then quench with water (1 mL) and purify with silica gel column chromatography (MeOH:DCM := 1 :50) to give AS as a solid (650 mg, 65percent yield). (MS: [M+H]+ 160.1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | <strong>[2164-66-1]2-Amino-4-methoxycarbonylpyrimidine</strong> (3.0g, 20mmol, Reference Compound No.3-1) was suspended in a mixture solvent of ethanol (150mL) and dichloromethane (20mL), then sodium borohydride (2.2g, 59mmol) was added thereto at room temperature, and the whole was stirred for 24 hours. Acetone (20mL) was added gradually under ice-cooling, and then 2M hydrochloric acid was added until the bubbles were no longer formed. Saturated aqueous sodium hydrogencarbonate solution was added to adjust the pH of the reaction mixture to 8, and the precipitated solid was filtered out. The filtrate was concentrated under reduced pressure, then suspended in a 10percent methanol-chloroform solution, and the mixture was filtered again with silica gel (5.0g). The filtrate was evaporated under reduced pressure, the precipitated solid was filterd off with ethyl acetate, and dried under reduced pressure to give 1.8g of the title Reference Compound as a pale yellow solid (Yield: 73percent) 1H-NMR (400MHz, DMSO-d6) delta 4.30(s,2H),5.35(s,1H),6.48(s,2H),6.65(d,J = 4.9 Hz,1H),8.19(d,J = 4.9 Hz,1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | 2-Amino-4-hydroxymethylpyrimidine (750mg,6.0mmol,Reference Compound No.4-1) and tert-butyldimethylsilyl chloride (990mg, 6.6mmol) were suspended in anhydrous N,N-dimethylformamide (8.0mL), then imidazole (0.90g, 13mmol) was added thereto and the mixture was stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate (50mL), washed twice with saturated aqueous sodium hydrogencarbonate solution (50mL), and then washed with brine (50mL), and dried over anhydrous magnesium sulfate. Then the solvent was evaporated under reduced pressure, the precipitated solid was filtered off with 50percent ethyl acetate-n-hexane solution, and dried under reduced pressure to give 1.2g of the title Reference Compound as a white solid (Yield: 84percent). 1H-NMR(400MHz,CDCl3) delta 0.11(s,6H),0.95(s,9H),4.59(s,2H),5.03(s,2H),6.87(d,J = 5.1 Hz,1H),8.29(d,J = 5.1 Hz,1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃; for 7h; | N,N-Diisopropylethylamine(490muL,2.9mmol) and methanesulfonyl chloride(110muL,1.5mmol) were added to a suspension of <strong>[2164-67-2]2-amino-4-hydroxymethylpyrimidine</strong> (170mg,1.3mmol, Reference Compound No.4-1) in anhydrous tetrahydrofuran (5.0 mL) under ice-cooling, and the mixture was stirred for 7 hours at room temperature. The reaction mixture was diluted with ethyl acetate (300mL), washed with water (300mL), and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the precipitated solid was filtered off with ethyl acetate, and dried under reduced pressure to give 140mg of the title Reference Compound as a white solid (Yield: 53percent). 1H-NMR(500MHz, DMSO-d6) delta 3.30(s,3H),5.06(s,2H),6.63(d,J = 5.2 Hz,1H),6.78(s,2H),8.28(d,J = 5.2 Hz, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | With hydrogenchloride; sodium tetrahydroborate; NaOH; In tetrahydrofuran; methanol; water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; | Intermediate P: 1-(4-((2-Aminopyrimidin-4-yl)methoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureaHydrochloric acid (2M, 207 mL, 414 mmol) was added to 4-(dimethoxymethyl)pyrimidin-2-amine (68) (WO 2007/096764) (14.0 g, 83 mmol) and the mixture heated at 48° C. for 16 hr.The mixture was cooled to RT and was neutralized with solid Na2CO3 which produced a precipitate at pH 7.The suspension was diluted with EtOAc (300 mL) and the solid removed by filtration.The organic layer was separated and the aqueous layer was extracted with 1percent MeOH in THF (4*300 mL).The organics were combined, dried and then evaporated in vacuo.The residue (ca. 4.0 g) was suspended in a mixture of MeOH (100 mL), THF (100 mL) and water (100 mL) and treated with NaBH4 (1.57 g, 41.4 mmol).After stirring for 1 hr a solution of NaOH (1M, 20 mL) was added and the mixture was allowed to stand at RT for 48 hr.The solvents were evaporated to give a yellow solid which was partitioned between water (50 mL) and EtOAc (100 mL).The solid which formed at the interface was removed by filtration and the aq layer was extracted with THF (3*300 mL) then dried and evaporated to give a yellow solid.The material was suspended in THF (100 mL) and MeOH (50 mL) and absorbed onto silica gel (20 g) and subjected to column chromatography (80 g, 15percent MeOH in DCM isocratic elution) to give (2-aminopyrimidin-4-yl)methanol (69) as an off-white solid (720 mg, 7percent): m/z 126 (M+H)+ (ES+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -50 - 20℃; for 1.08333h; | To a stirred mixture of (69) (700 mg, 3.92 mmol), 4-nitronaphthol (2) (741 mg, 3.92 mmol) and PPh3 (1.23 g, 4.70 mmol) in THF (20 mL) under nitrogen at ?50° C. was added DIAD (996 muL, 4.70 mmol) dropwise over 5 min. The mixture was allowed to warm to RT and stirred for 1 hr during which time a yellow precipitate formed. The suspension was stirred overnight and the volatiles were evaporated in vacuo. The residue was triturated from MeOH (50 mL) and the pale yellow solid collected by filtration and washed with diethyl ether (50 mL) to give 4-((4-nitronaphthalen-1-yloxy)methyl)pyrimidin-2-amine (70) (1.10 g, 93percent): m/z 297 (M+H)+ (ES+). |
With DIAD; triphenylphosphine; In tetrahydrofuran; methanol; | To a stirred mixture of (69) (700 mg, 3.92 mmol), 4-nitronaphthol (2) (741 mg, 3.92 mmol) and PPh3 (1.23 g, 4.70 mmol) in THF (20 mL) under nitrogen at -50° C. was added DIAD (996 muL, 4.70 mmol) dropwise over 5 min.The mixture was allowed to warm to RT and stirred for 1 hr during which time a yellow precipitate formed.The suspension was stirred overnight and the volatiles were evaporated in vacuo.The residue was triturated from MeOH (50 mL) and the pale yellow solid collected by filtration and washed with diethyl ether (50 mL) to give 4-((4-nitronaphthalen-1-yloxy)methyl)pyrimidin-2-amine (70) (1.10 g, 93percent): m/z 297 (M+H)+ (ES+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate; potassium carbonate; at 0 - 5℃; for 0.5h;pH 8.0; | The solution of 5.01 g 4-(dimethoxymethyl)pyrimidin-2-amine (29.5 mmol) in 100 mL 2Naq. HCI was stirred at 60°C for 5h. Reaction mixture was cooled to 0°C, then 7.60 g NaOH(190 mmol) was added portionwise. The pH was adjusted to 8 using 10percent K2C03 solution, then 2.24 g sodium borohydride (59.0 mmol) was added portionwise keeping the temperature under 5°C and stirred for 30 mm at 0°C. The reaction mixture was extracted with EtOAc, the combined organic phases were dried over Na2SO4 and concentrated underreduced pressure. The crude product was purified via flash chromatography (MeOH - containing I percentN113- and DCM).?FT NMR (400 MHz, DMSO-d5): 8,20 (d, 111), 6.66 (d, 111), 6.49 (br s, 211), 5.35 (t, IH), 4.30 (d, 211). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | Hydrochloric acid (2M, 207 mL, 414 mmol) was added to 4-(dimethoxymethyl)pyrimidin-2-amine (68) (WO 2007/096764) (14.0 g, 83 mmol) and the mixture heated at 48° C. for 16 hr. The mixture was cooled to RT and was neutralized with solid Na2CO3 which produced a precipitate at pH 7. The suspension was diluted with EtOAc (300 mL) and the solid removed by filtration. The organic layer was separated and the aqueous layer was extracted with 1percent MeOH in THF (4×300 mL). The organics were combined, dried and then evaporated in vacuo. The residue (ca. 4.0 g) was suspended in a mixture of MeOH (100 mL), THF (100 mL) and water (100 mL) and treated with NaBH4 (1.57 g, 41.4 mmol). After stirring for 1 hr a solution of NaOH (1M, 20 mL) was added and the mixture was allowed to stand at RT for 48 hr. The solvents were evaporated to give a yellow solid which was partitioned between water (50 mL) and EtOAc (100 mL). The solid which formed at the interface was removed by filtration and the aq layer was extracted with THF (3×300 mL) then dried and evaporated to give a yellow solid. The material was suspended in THF (100 mL) and MeOH (50 mL) and absorbed onto silica gel (20 g) and subjected to column chromatography (80 g, 15percent MeOH in DCM isocratic elution) to give (2-aminopyrimidin-4-yl)methanol (69) as an off-white solid (720 mg, 7percent): m/z 126 (M+H)+ (ES+). |
A376727 [74502-82-2]
(6-Methylpyrimidin-4-yl)methanol
Similarity: 0.73
A407883 [2164-65-0]
2-Aminopyrimidine-4-carboxylic acid
Similarity: 0.81
A111199 [165807-05-6]
4-Dimethoxymethylpyrimidin-2-ylamine
Similarity: 0.80
A407883 [2164-65-0]
2-Aminopyrimidine-4-carboxylic acid
Similarity: 0.81
A111199 [165807-05-6]
4-Dimethoxymethylpyrimidin-2-ylamine
Similarity: 0.80