[ CAS No. 31462-58-5 ] {[proInfo.proName]}

Name: 31462-58-5|5-Iodopyrimidine|98%
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Quality Control of [ 31462-58-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 31462-58-5 ]

Product Details of [ 31462-58-5 ]

CAS No. :	31462-58-5	MDL No. :	MFCD00233961
Formula :	C₄H₃IN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DNWRLMRKDSGSPL-UHFFFAOYSA-N
M.W :	205.98	Pubchem ID :	1201421
Synonyms :

Calculated chemistry of [ 31462-58-5 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.75
TPSA :	25.78 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.46
Log Po/w (XLOGP3) :	0.85
Log Po/w (WLOGP) :	1.08
Log Po/w (MLOGP) :	0.54
Log Po/w (SILICOS-IT) :	2.06
Consensus Log Po/w :	1.2

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.29
Solubility :	1.06 mg/ml ; 0.00517 mol/l
Class :	Soluble
Log S (Ali) :	-0.97
Solubility :	21.8 mg/ml ; 0.106 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.61
Solubility :	0.508 mg/ml ; 0.00247 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.71

Safety of [ 31462-58-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 31462-58-5 ]

* 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.

Upstream synthesis route of [ 31462-58-5 ]
Downstream synthetic route of [ 31462-58-5 ]

[ 31462-58-5 ] Synthesis Path-Upstream 1~5

1
[ 289-95-2 ]
[ 2426-94-0 ]
[ 31462-58-5 ]

Reference： [1] Journal of Organic Chemistry, 2007, vol. 72, # 17, p. 6602 - 6605

2
[ 4595-59-9 ]
[ 31462-58-5 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 15, p. 3974 - 3977
[2] Journal of the American Chemical Society, 2015, vol. 137, # 26, p. 8328 - 8331

3
[ 289-95-2 ]
[ 31462-58-5 ]

Reference： [1] Chemistry - A European Journal, 2010, vol. 16, # 27, p. 8191 - 8201
[2] Tetrahedron Letters, 2011, vol. 52, # 36, p. 4590 - 4594

4
[ 289-95-2 ]
[ 2426-94-0 ]
[ 31462-58-5 ]

Reference： [1] Journal of Organic Chemistry, 2007, vol. 72, # 17, p. 6602 - 6605

5
[ 289-95-2 ]
[ 31462-58-5 ]

Reference： [1] Heterocycles, 2008, vol. 76, # 2, p. 1057 - 1060
[2] Patent: US4507302, 1985, A,

[ 31462-58-5 ] Synthesis Path-Downstream 1~63

1
[ 110-00-9 ]
[ 31462-58-5 ]
[ 63558-71-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1977,p. 621 - 624

2
[ 188290-36-0 ]
[ 31462-58-5 ]
[ 58759-01-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1977,p. 621 - 624

3
[ 188290-36-0 ]
[ 31462-58-5 ]
[ 58759-01-6 ]
[ 58759-02-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1977,p. 621 - 624

4
[ 108-24-7 ]
[ 130377-86-5 ]
[ 31462-58-5 ]
2-Butyl-3-(5-pyrimidyl)-5-methoxy-6-methyl-1,4-diacetoxybenzene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 408 - 413

5
[ 130352-56-6 ]
[ 31462-58-5 ]
2,3,6-Trimethyl-5-(5-pyrimidyl)-1,4-benzoquinone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 408 - 413

6
[ 130352-65-7 ]
[ 31462-58-5 ]
2-(Trimethylsilyl)-3-(5-pyrimidyl)-1,4-naphthoquinone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 408 - 413

8
[(triisopropylsilanyl)-ethynyl]-phosphonic acid diethyl ester [ No CAS ]
[ 31462-58-5 ]
pyrimidin-5-ylethynyl-phosphonic acid diethyl ester [ No CAS ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 1301 - 1311

9
[ 289-95-2 ]
4-iodopyrimidine [ No CAS ]
[ 2426-94-0 ]
[ 31462-58-5 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 6602 - 6605

10
[ 289-95-2 ]
[ 31462-58-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N-iodo-succinimide; In ethanol; acetic acid;	Iodination (X3 =I) To 1.95 mM of the appropriate pyrimidine was added 25.0 ml. of glacial acetic acid and 434 mg. (2 mM) of N-iodosuccinimide. The reaction mixture was allowed to stir at ambient temperature for 5 days. The mixture was evaporated to dryness under vacuum at 50 C. The solids were purified by heating with 50 ml. of absolute ethanol at reflux and cooling to room temperature. Filtering and washing with absolute ethanol gave the pure 5-iodopyrimidine.

Reference： [1]Heterocycles,2008,vol. 76,p. 1057 - 1060
[2]Patent: US4507302,1985,A

11
2-(3,4-dimethoxyphenyl)ethylcarbonyloxy-Merrifield resin [ No CAS ]
[ 31462-58-5 ]
{2-[N-Boc-N-trimethylsilylamino]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene}-bis(η⁵-cyclopentadienyl)titanium [ No CAS ]
[ 1007351-79-2 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 901 - 914

12
2-(3-pyridyl)ethylcarbonyloxy-Merrifield resin [ No CAS ]
[ 31462-58-5 ]
{2-[N-Boc-N-trimethylsilylamino]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene}-bis(η⁵-cyclopentadienyl)titanium [ No CAS ]
[ 1007351-55-4 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 901 - 914

13
2-(N-Boc-piperidin-4-yl)ethylcarbonyloxy-Merrifield resin [ No CAS ]
[ 31462-58-5 ]
{2-[N-Boc-N-trimethylsilylamino]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene}-bis(η⁵-cyclopentadienyl)titanium [ No CAS ]
[ 1007351-89-4 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 901 - 914

14
3-phenoxypropylcarbonyloxy-Merrifield resin [ No CAS ]
[ 31462-58-5 ]
{2-[N-Boc-N-trimethylsilylamino]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene}-bis(η⁵-cyclopentadienyl)titanium [ No CAS ]
[ 1007351-67-8 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 901 - 914

15
3-phenylpropylcarbonyloxy-Merrifield resin [ No CAS ]
[ 31462-58-5 ]
{2-[N-Boc-N-trimethylsilylamino]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene}-bis(η⁵-cyclopentadienyl)titanium [ No CAS ]
[ 1007351-44-1 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 901 - 914

16
n-propylcarbonyloxy-Merrifield resin [ No CAS ]
[ 31462-58-5 ]
{2-[N-Boc-N-trimethylsilylamino]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene}-bis(η⁵-cyclopentadienyl)titanium [ No CAS ]
[ 1007351-33-8 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 901 - 914

17
phenethylcarbonyloxy-Merrifield resin [ No CAS ]
[ 31462-58-5 ]
{2-[N-Boc-N-trimethylsilylamino]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene}-bis(η⁵-cyclopentadienyl)titanium [ No CAS ]
[ 1007351-23-6 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 901 - 914

18
[ 31462-58-5 ]
[ 301673-14-3 ]
[ 1019206-22-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 994 - 998

19
[ 5049-61-6 ]
[ 31462-58-5 ]
[ 1148035-10-2 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 5766 - 5768

20
[ 31462-58-5 ]
5-ethyl-3-(3-tributylstannyl)-2,5-dihydrofuran-2-one [ No CAS ]
[ 1206522-11-3 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,2009,vol. 74,p. 1161 - 1178

21
[ 904685-31-0 ]
[ 31462-58-5 ]
C₂₆H₂₀ClN₅O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2068 - 2073

22
[ 289-95-2 ]
4-iodopyrimidine [ No CAS ]
[ 31462-58-5 ]

Yield	Reaction Conditions	Operation in experiment
		[Li(TMP)Zn(tBu)2] 1 was made according to the literature procedure2 on a 0.4 mmol scale in THF solution. To this solution pyrimidine (32 mg, 0.4 mmol) was added at 0C and the bright red/orange solution allowed to stir for 1 hour. Next the solution was quenched with I2 (508 mg, in 1 mL THF) and allowed to stir for 1 hour. A 10% solution of Na2S2O3 was added until bleaching and the product extracted with DCM (3 x 1 mL). The combined organic extracts were dried over MgSO4 and the solvent removed under reduced pressure. The residue was analysed by NMR spectroscopy to show a mixture (70:30) of 4-iodo and 5-iodopyrimidine. 1H NMR (400 MHz,CDCl3) delta ppm 7.62 (dd, 1 H) 8.19 (d, 1 H) 8.83 (d, 1 H) 8.67 (s, 2 H) 8.91 (s, 1 H). Values consistent with previous data reported in the literature.

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 8191 - 8201
[2]Tetrahedron Letters,2011,vol. 52,p. 4590 - 4594

23
[ 98-91-9 ]
[ 31462-58-5 ]
[ 1269071-46-6 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 820 - 823

24
[ 73652-14-9 ]
[ 31462-58-5 ]
[ 1370725-03-3 ]

Reference： [1]Synlett,2012,p. 443 - 447

25
[ 1363441-17-1 ]
[ 31462-58-5 ]
[ 1363430-78-7 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; N,N-dimethylglycine hydrochoride; caesium carbonate; In 1,4-dioxane; at 90℃; for 2h;	Example 10.1 (general route) N- 1 -(4-((4-(Pyrimidin-5-yloxy)phenyl)ethynyl)phenyl)propan-2-yl)acetam28.1 mg (0.14 mmol) <strong>[31462-58-5]5-iodopyrimidine</strong>, 40.0 mg (0.14 mmol) N-(1 -(4-((4-hydroxy- phenyl)ethynyl)phenyl)propan-2-yl)acetamide (176.1 ), 1 .30 mg (0.07 mmol) Cul, 1 .9 mg (0.14 mmol) Nu, Nu-dimethylglycine hydrochloride and 58.7 mg (0.18 mmol) CS2CO3 are added to 1 ml_ dioxane. The reaction mixture is stirred at 90C for 2 h then filtered through a plug of silica gel and washed with DMF. The filtrate is purified by HPLC (MeOH/H20/TFA).C23H21 N3O2 (M= 371 .4 g/mol)ESI-MS: 372 [M+H]+ Rt (HPLC): 2.22 min (method M)
	With copper(l) iodide; N,N-dimethylglycine hydrochoride; caesium carbonate; In 1,4-dioxane; at 90℃; for 2h;	Example 10; Example 10.1; General Route; N-(1-(4-((4-(Pyrimidin-5-yloxy)phenyl)ethynyl)phenyl)propan-2-yl)acetamide; 28.1 mg (0.14 mmol) <strong>[31462-58-5]5-iodopyrimidine</strong>, 40.0 mg (0.14 mmol) N-(1-(4-((4-hydroxy-phenyl)ethynyl)phenyl)propan-2-yl)acetamide (I76.1), 1.30 mg (0.07 mmol) CuI, 1.9 mg (0.14 mmol) N,N-dimethylglycine hydrochloride and 58.7 mg (0.18 mmol) Cs2CO3 are added to 1 mL dioxane. The reaction mixture is stirred at 90 C. for 2 h then filtered through a plug of silica gel and washed with DMF. The filtrate is purified by HPLC (MeOH/H2O/TFA).C23H21N3O2 (M=371.4 g/mol)ESI-MS: 372 [M+H]+ Rt (HPLC): 2.22 min (method M)

Reference： [1]Patent: WO2012/28676,2012,A1 .Location in patent: Page/Page column 205-206
[2]Patent: US2012/214785,2012,A1 .Location in patent: Page/Page column 131-132

26
[ 1275608-03-1 ]
[ 31462-58-5 ]
[ 1425309-81-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1529 - 1536

27
[ 31462-58-5 ]
[ 873398-85-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With carbon disulfide; 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate; In neat (no solvent); at 100℃; for 0.0833333h;Microwave irradiation; Sealed tube;	General procedure: A sealed 10 mL glass tube containing aryl halide (1 mmol), CS2(0.5 mmol) and [DBUH]+[OAc]- (1 mL) was placed in the cavity of a microwave reactor and irradiated for 5-60 min at 100-120 C and power 150 W. After cooling to room temperature, the reaction mixture was extracted with Et2O (3 × 5 mL) and the [DBUH]+[OAc]-was separated from the product. The organic layers were combined and the solvent removed under reduced pressure to provide the crude product, which was further purified by column chromatography on silica gel using petroleum ether/EtOAc as the eluent. The recovered [DBUH]+[OAc]- was washed with diethyl ether and could be reused in the next reaction. All of the products are known compounds and their characterisation data were compared and are consistent with literature reports.

Reference： [1]Journal of Chemical Research,2016,vol. 40,p. 305 - 307
[2]Advanced Synthesis and Catalysis,2013,vol. 355,p. 2297 - 2307

28
[ 1586035-32-6 ]
[ 31462-58-5 ]
[ 1586035-44-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 2344 - 2348

29
[ 5720-07-0 ]
[ 31462-58-5 ]
[ 69491-47-0 ]