Home Cart Sign in  
Chemical Structure| 2164-66-1 Chemical Structure| 2164-66-1

Structure of 2164-66-1

Chemical Structure| 2164-66-1

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

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

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 2164-66-1 ]

CAS No. :2164-66-1
Formula : C6H7N3O2
M.W : 153.14
SMILES Code : O=C(C1=NC(N)=NC=C1)OC
MDL No. :MFCD16657647
InChI Key :IHGOYDMXENEUOO-UHFFFAOYSA-N
Pubchem ID :57971148

Safety of [ 2164-66-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 2164-66-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.17
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 37.72
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

78.1 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.18
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.04
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.15
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.63
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.02
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.09

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.09
Solubility 12.6 mg/ml ; 0.082 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.23
Solubility 8.96 mg/ml ; 0.0585 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.35
Solubility 6.78 mg/ml ; 0.0443 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.21 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.75

Application In Synthesis of [ 2164-66-1 ]

* 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.

  • Downstream synthetic route of [ 2164-66-1 ]

[ 2164-66-1 ] Synthesis Path-Downstream   1~10

  • 3
  • [ 502164-18-3 ]
  • [ 50-01-1 ]
  • [ 2164-66-1 ]
YieldReaction ConditionsOperation in experiment
60% With triethylamine; In propiononitrile; at 100.0℃; for 4.0h; Triethylamine (29mL, 210mmol) was added to a suspension of methyl 4-butoxy-2-oxo-3-butenate (37g, 200mmol,) and guanidine hydrochloride (23 g, 240 mmol) in propionitrile (50mL), and the mixture was stirred for 4 hours at 100C. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give 18g as the mixture of the title Reference Compound and the butyl ester form of the title Reference compound as a gray-white solid (Yield: 60%). 1H-NMR (500MHz, DMSO-d6) delta 3.85(s,3H),6.99-7.06(m,3H),8.48(d,J = 4.8 Hz,1H)
  • 4
  • [ 2164-66-1 ]
  • [ 2164-67-2 ]
YieldReaction ConditionsOperation 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)
  • 5
  • [ 195447-83-7 ]
  • [ 2164-66-1 ]
  • [ 1018318-12-1 ]
YieldReaction ConditionsOperation in experiment
Step A: Preparation of 2-[[[3-(l,l-dimethylethyl)-l-ethyl-lH-pyrazol-5-yl]carbonyl]ammo]-4- pyrimidinecarboxylic acidTo a solution of 3-(l,l-dimethylethyl)-l-ethyl-lH-pyrazol-5-carboxylic acid (12.8 g, 65mmol) in DCM (100 ml) were added oxalyl chloride (16 g, 131 mmol) and DMF (3 drops). <n="36"/>- 35 -The solution was stirred for 1.5 h and the solvent and excess oxalyl chloride removed under reduced pressure.The resulting residue was taken up in DCM (25 ml) and added to a well stirred mixture of <strong>[2164-66-1]methyl 2-amino-4-pyrimidinecarboxylate</strong> (5.0 g, 33 mmol), triethylamine (18.2 ml, 131 5 mmol) and DMAP (0.2g) in DCM (125 ml) and then stirred overnight at 2O0C and heated under reflux for 2 h. The reaction mixture was cooled to room temperature, poured into water (100 ml), extracted with DCM (2 x 70 ml) and the extracts dried over anhydrous magnesium sulphate. Removal of the solvent gave the residue as a gum. The gum was taken up in a mixture of sodium hydroxide (7.0 g) and methanol (75 ml) and the10 mixture stirred for 3 h at 2O0C. The solvent was removed and the residue partitioned between water (300 ml) and ethyl acetate. The aqueous phase was neutralised with c. HCl, the precipitate extracted into DCM, dried over anhydrous magnesium sulphate. Removal of the solvent gave a crude residue which was washed with DCM (30 ml) for 10 min at 200C and filtered to give the title acid as a white solid (0.7g). This was used in the next step without15 further purification .
  • 6
  • [ 2164-66-1 ]
  • [ 79583-19-0 ]
  • methyl 2-(1-methyl-1H-pyrazole-4-carboxamido)pyrimidine-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With pyridine; at 20.0℃; Into a 100-mL round-bottom flask was placed a solution of methyl 2- aminopyrimidine-4-carboxylate (1 g, 6.53 mmol, 1.00 equiv) in pyridine (20 mL), and 1- methyl-1H-pyrazole-4-carbonyl chloride (1 g, 6.92 mmol, 1.05 equiv). The resulting solution was stirred overnight at room temperature then concentrated under vacuum. The residue was applied onto a silica gel column and eluted with dichloromethane/methanol (20:1). This resulted in 1 g (59%) of methyl 2-(1-methyl-1H-pyrazole-4-amido)pyrimidine-4-carboxylate as a white solid.
  • 7
  • [ 2164-66-1 ]
  • methyl 2-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-8-carboxylate [ No CAS ]
  • 8
  • [ 2164-66-1 ]
  • [ 70-11-1 ]
  • [ 131862-26-5 ]
YieldReaction ConditionsOperation in experiment
66% In butanone; at 85.0℃; Into a 250-mL round-bottom flask, was placed methyl 2-aminopyridine-3- carboxylate (1 g, 6.57 mmol, 1.00 equiv), 2-butanone (80 mL), and 2-bromo-1-phenylethan-1- one (1.5 g, 7.54 mmol, 1.10 equiv). The resulting solution was stirred overnight at 85 oC then concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:3). This resulted in 1.1 g (66%) of methyl 2- phenylimidazo[1,2-a]pyridine-8-carboxylate as a light brown solid.
  • 9
  • [ 2164-66-1 ]
  • 2-[[[3-(1,1-dimethylethyl)-1-ethyl-1H-pyrazol-5-yl]carbonyl]amino]-4-pyrimidylcarbonyl-(3,3-difluoroazetidine) [ No CAS ]
  • 10
  • [ 2164-66-1 ]
  • [ 1010839-51-6 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 2164-66-1 ]

Esters

Chemical Structure| 62846-82-6

A318634 [62846-82-6]

Ethyl 4-pyrimidinecarboxylate

Similarity: 0.87

Chemical Structure| 1034737-23-9

A296600 [1034737-23-9]

Methyl 2-amino-5-bromopyrimidine-4-carboxylate

Similarity: 0.82

Chemical Structure| 1207954-85-5

A193870 [1207954-85-5]

Ethyl 2-bromopyrimidine-4-carboxylate

Similarity: 0.77

Chemical Structure| 6627-22-1

A247927 [6627-22-1]

Methyl 6-chloropyrimidine-4-carboxylate

Similarity: 0.77

Chemical Structure| 149849-94-5

A279800 [149849-94-5]

Methyl 2-chloropyrimidine-4-carboxylate

Similarity: 0.77

Amines

Chemical Structure| 2164-65-0

A407883 [2164-65-0]

2-Aminopyrimidine-4-carboxylic acid

Similarity: 0.90

Chemical Structure| 1034737-23-9

A296600 [1034737-23-9]

Methyl 2-amino-5-bromopyrimidine-4-carboxylate

Similarity: 0.82

Chemical Structure| 944129-00-4

A153855 [944129-00-4]

Methyl 6-amino-2-chloropyrimidine-4-carboxylate

Similarity: 0.74

Chemical Structure| 165807-05-6

A111199 [165807-05-6]

4-Dimethoxymethylpyrimidin-2-ylamine

Similarity: 0.74

Chemical Structure| 914208-48-3

A140853 [914208-48-3]

2-Amino-5-bromopyrimidine-4-carboxylic acid

Similarity: 0.74

Related Parent Nucleus of
[ 2164-66-1 ]

Pyrimidines

Chemical Structure| 2164-65-0

A407883 [2164-65-0]

2-Aminopyrimidine-4-carboxylic acid

Similarity: 0.90

Chemical Structure| 62846-82-6

A318634 [62846-82-6]

Ethyl 4-pyrimidinecarboxylate

Similarity: 0.87

Chemical Structure| 1034737-23-9

A296600 [1034737-23-9]

Methyl 2-amino-5-bromopyrimidine-4-carboxylate

Similarity: 0.82

Chemical Structure| 31462-59-6

A193086 [31462-59-6]

Pyrimidine-4-carboxylic acid

Similarity: 0.80

Chemical Structure| 1207954-85-5

A193870 [1207954-85-5]

Ethyl 2-bromopyrimidine-4-carboxylate

Similarity: 0.77