Home Cart Sign in  
Chemical Structure| 4349-07-9 Chemical Structure| 4349-07-9

Structure of 4349-07-9

Chemical Structure| 4349-07-9

*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 [ 4349-07-9 ]

CAS No. :4349-07-9
Formula : C4H3IN2O
M.W : 221.98
SMILES Code : IC1=CN=CN=C1O
MDL No. :MFCD02666079
InChI Key :SMIGOGPUTQXOKF-UHFFFAOYSA-N
Pubchem ID :12356582

Safety of [ 4349-07-9 ]

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

Computational Chemistry of [ 4349-07-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 36.77
TPSA ?

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

46.01 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.35
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

0.83
Log Po/w (WLOGP)?

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

0.79
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.

0.33
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

1.55
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.97

Water Solubility

Log S (ESOL):?

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

-2.29
Solubility 1.13 mg/ml ; 0.00508 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-1.38
Solubility 9.28 mg/ml ; 0.0418 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

-2.04
Solubility 2.05 mg/ml ; 0.00923 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

Yes
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.

-7.06 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

1.0 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)

1.92

Application In Synthesis of [ 4349-07-9 ]

* 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 [ 4349-07-9 ]

[ 4349-07-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 4349-07-9 ]
  • [ 63558-65-6 ]
YieldReaction ConditionsOperation in experiment
88% With oxalyl dichloride; N,N-dimethyl-formamide; In 1,2-dichloro-ethane; for 3h;Heating / reflux; To a stirred solution containing 7.7 mL (99 MMOL) of DMF and 150 mL of DICHLOROETHANE at 0C was added 12.7 mL (144.6 MMOL) of OXALYL chloride slowly to control vigorous gas evolution. After the evolution of gas had ceased, 10.0 g of iodopyrimidone was added and the reaction mixture was heated at reflux for 3h, then cooled to room temperature and partitioned between water and DICHLOROMETHANE. The organic layers were dried over MGS04 and the solvent was removed under reduced pressure to give 9.6 g (88%) of the title COMPOUND. 1H-NMR (300 MHz, CDCI3) A 8. 89 (s, 1H) and 8.98 (s, 1H) ; ESIMS : 241.1 (M+H)+
83% With oxalyl dichloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; for 2h;Reflux; Oxalyl chloride (1 .27 ml, 14.61 mmol) was added dropwise in 707 ml dimethylformamide and 20 ml dichloroethane. 5-lodopyrimidin-4(3/-/)-one ( 1 g, 4.55 mmol) was added and the reaction was heated at reflux for 2 h. The reaction mixture was dissolved in dichloromethane, washed with water, dried over sodium sulphate, filtered and concentrated under reduced pressure to give 0.91 g (83 % yield) of the title compound as a solid. Purity 100%.LRMS (m/z): 241 (M+1 )+
75.9% With oxalyl dichloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; at 0 - 85℃; for 4h; N,N-dimethylformamide (3.9 mL, 27.0 mmol) was dissolved in 1,2-dichloroethane (90 mL) at 0 C, the reaction was stirred for 10 min, and oxalyl chloride (6.8 mL, 27.0 mmol) was added dropwise. ),After 20 minutes of dropwise addition, 5-iodopyrimidine-4(3H)one (5.0 g, 22.5 mmol) was added.The temperature was raised to 85 C for 4.0 h, and the reaction solution was concentrated.The residue was dissolved in dichloromethane (120 mL).The organic phase was washed with saturated brine (20 mL×2).Dry anhydrous sodium sulfate (20g),Filter and concentrate to give 4.1 g of a brown oil.The yield was 75.9%. The product was directly subjected to the next reaction without purification.
With trichlorophosphate; In methanol; water; toluene; Method V Preparation of 4-Chloro-5-iodopyrimidine 5-Iodo-4(3H)-pyrimidinone (1 eq.) was suspended in toluene to which was added POCl3 (2.0 eq.). The reaction mixture was heated to reflux for 3 hours, and then cooled and concentrated. The residue was suspended in water, adjusted to pH=7 by addition of 4N sodium hydroxide, and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4), filtered and stripped to give a red oil. The crude product was dissolved in methanol and silica gel was added. Following concentration, the coated silica gel was loaded onto a plug of silica gel and elution with ethyl acetate/hexanes yielded the title compound.
With trichlorophosphate; In toluene; for 3h;Heating / reflux; Method 0 Preparation of 4-Chloro-5-iodopyrimidine 5-Iodo-4(3H)-pyrimidinone (1 eq. ) was suspended in toluene to which was added POC13 (2.0 eq. ). The reaction mixture was heated to reflux for 3 hours, and then cooled and concentrated. The residue was suspended in water, adjusted to pH=7 by addition of 4N sodium hydroxide, and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgS04), filtered and stripped to give a red oil. The crude product was dissolved in methanol and silica gel was added. Following concentration, the coated silica gel was loaded onto a plug of silica gel and elution with ethyl acetate/hexanes yielded the title compound.

  • 2
  • [ 4349-07-9 ]
  • [ 63558-65-6 ]
YieldReaction ConditionsOperation in experiment
Step 2. Preparation of 4-chloro-5-iodopirnidine; A mixture of 5-iodopyrimidin-4-ol (14.9 g, 67.1 mmol) in phosphorous oxychloride (25.0 ml, 268 mmol) with a water-cooled reflux condenser fitted with a drying tube was heated to reflux in a 135 C. bath for 3 h. The purple solution was cooled until warm and poured onto ice with swirling. The ice-cold mixture was basified with 6N NaOH, with addition of ice to maintain the cool temperature. The resulting brown precipitate was collected by filtration, rinsed with water, and dried in vacuo to give 4-chloro-5-iodopyrimidine as an orange solid. MS m/z=241 [M+H]+. Calc'd for C4H2IClN2: 240.4.
4 g With oxalyl dichloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; at 0 - 85℃; for 5h; At 0 C,N,N-dimethylformamide (2.0 g, 27.0 mmol) was dissolved in 1,2-dichloroethane (60 mL), and stirred for 30 min.Oxalyl chloride (3.4 g, 27.0 mmol) was slowly added dropwise, and after the addition was completed,The solution is viscous,Add compound 4-hydroxy-5-iodopyrimidine(5g, 22.5mmol),The temperature was slowly raised to 85 C and the reaction was stirred for 5.0 h. concentrate,The residue was dissolved in dichloromethane (70 mL).The organic phase was washed once with distilled water (30 mL).Dry anhydrous sodium sulfate (12g), concentrated,4.0 g of a reddish brown oil was obtained, which was directly subjected to the next reaction.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 4349-07-9 ]

Alcohols

Chemical Structure| 51953-18-5

A136378 [51953-18-5]

Pyrimidin-4-ol

Similarity: 0.73

Chemical Structure| 17758-52-0

A273168 [17758-52-0]

4-Hydroxy-5-methylpyrimidine

Similarity: 0.65

Chemical Structure| 67383-35-1

A151324 [67383-35-1]

2-Methylpyrimidin-4-ol

Similarity: 0.63

Chemical Structure| 1193-24-4

A394800 [1193-24-4]

4,6-Dihydroxypyrimidine

Similarity: 0.60

Chemical Structure| 29939-37-5

A193465 [29939-37-5]

4-Hydroxy-6-hydrazinylpyrimidine

Similarity: 0.60

Related Parent Nucleus of
[ 4349-07-9 ]

Pyrimidines

Chemical Structure| 219915-13-6

A207026 [219915-13-6]

5-Iodo-4-methoxypyrimidine

Similarity: 0.91

Chemical Structure| 89322-66-7

A129201 [89322-66-7]

2-Amino-5-iodo-4-methoxypyrimidine

Similarity: 0.80

Chemical Structure| 52522-99-3

A119284 [52522-99-3]

5-Iodo-2,4-dimethoxypyrimidine

Similarity: 0.77

Chemical Structure| 51953-18-5

A136378 [51953-18-5]

Pyrimidin-4-ol

Similarity: 0.73

Chemical Structure| 31462-58-5

A308425 [31462-58-5]

5-Iodopyrimidine

Similarity: 0.73