[ CAS No. 53557-69-0 ] {[proInfo.proName]}

Name: 53557-69-0|6-Iodopyrimidin-4-amine|97%
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SKU: A325995
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Quality Control of [ 53557-69-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 53557-69-0 ]

SDS Specification

Alternatived Products of [ 53557-69-0 ]

Product Details of [ 53557-69-0 ]

CAS No. :	53557-69-0	MDL No. :	MFCD11109819
Formula :	C₄H₄IN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LQSJUQMCZHVKES-UHFFFAOYSA-N
M.W :	221.00	Pubchem ID :	12258871
Synonyms :

Calculated chemistry of [ 53557-69-0 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.15
TPSA :	51.8 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) :	-7.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	0.48
Log Po/w (WLOGP) :	0.67
Log Po/w (MLOGP) :	0.33
Log Po/w (SILICOS-IT) :	1.31
Consensus Log Po/w :	0.85

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.07
Solubility :	1.89 mg/ml ; 0.00856 mol/l
Class :	Soluble
Log S (Ali) :	-1.14
Solubility :	16.1 mg/ml ; 0.0729 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.25
Solubility :	1.24 mg/ml ; 0.00561 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.28

Safety of [ 53557-69-0 ]

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 [ 53557-69-0 ]

* 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 [ 53557-69-0 ]
Downstream synthetic route of [ 53557-69-0 ]

[ 53557-69-0 ] Synthesis Path-Upstream 1~5

1
[ 53557-69-0 ]
[ 7664-41-7 ]
[ 2434-56-2 ]

Reference： [1] Chemische Berichte, 1903, vol. 36, p. 2234

2
[ 5305-59-9 ]
[ 53557-69-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With hydrogen iodide; sodium iodide In water at 70℃; for 0.5 h;	Description 93; 6-IodoPvrimidin-4-amine-",; A mixture of 4-amino-6-chloropyrimidine [WO-A-0245652] (1. 00 g, 7.72 mmol), sodium iodide (5.79 g, 38.6 mmol) and 40percent HI (20 ml) were heated at 70°C for 30 min, then allowed to cool to room temperature. The precipitate was removed by filtration, and partitioned between dichloromethane and sat. NaHCO3. The organic layer was separated, and dried over Na2SO4, filtered, and evaporated to give the title compound (1.2 g, 70percent). 1H NMR (400 MHz, DMSO-d6) 6.89 (1 H, s), 7.04 (2 H, br s), 8.04 (1 H, s).
65%	With hydrogen iodide In water at 0 - 20℃; for 18.5 h;	6-Chloropyrimidin-4-ylamine (450 mg) was added in portions to HI (57percent wt. aq. , 20 mL) at 0 °C. The reaction mixture was stirred for 30 minutes at 0 °C and then at ambient temperature for 18 hours. The reaction mixture was treated with NaHC03 (sat. aq. ) until pH8 was achieved and then the product extracted with EtOAc (2 x 30 mL). The combined organics were washed with NaOH (2M, aq. ), dried (MgS04), filtered and then concentrated. The crude product was used directly without further purification (500 mg, 65percent); lH NMR (CDCl3) ; 6.90 (s, 1H), 7.03 (s, 2H), 8.05 (s, 1H); MS m/e MHs 221.
47%	With hydrogen iodide In water at 0 - 20℃; for 3 h;	General procedure: 2-Amino-4-chloropyrimidine (55) (13.0g, 100mmol) was added to a 57wt.percent aqueous solution of hydriodic acid (115ml, 1.00mol) at 0°C and the mixture was stirred at room temperature for 3h. The mixture was cooled to 0°C and the resulting precipitate was removed by filtration and taken up in cold 5N aqueous Na₂CO₃ (200ml). The mixture was extracted with EtOAc (3×500ml) and the combined organic layers were concentrated under reduced pressure to deliver 2-amino-4-iodopyrimidine (21.1g, 95.0mmol, 95percent yield) as a white solid.

Reference： [1] Patent: WO2005/47279, 2005, A1, . Location in patent: Page/Page column 50
[2] Patent: WO2005/60970, 2005, A1, . Location in patent: Page/Page column 124
[3] European Journal of Medicinal Chemistry, 2014, vol. 80, p. 364 - 382

3
[ 19646-06-1 ]
[ 53557-69-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 4, p. 1586 - 1605
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 17, p. 3639 - 3648

4
[ 1159818-57-1 ]
[ 53557-69-0 ]

Reference： [1] Patent: WO2016/71214, 2016, A1, . Location in patent: Page/Page column 84-85
[2] Patent: WO2018/206348, 2018, A1, . Location in patent: Page/Page column 54

5
[ 10132-07-7 ]
[ 53557-69-0 ]

Reference： [1] Chemische Berichte, 1903, vol. 36, p. 2234