[ CAS No. 695-85-2 ] {[proInfo.proName]}

Name: 695-85-2|4-Chloro-5-methoxypyrimidine|98%
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SKU: A113474
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Quality Control of [ 695-85-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 695-85-2 ]

SDS Specification

Alternatived Products of [ 695-85-2 ]

Product Details of [ 695-85-2 ]

CAS No. :	695-85-2	MDL No. :	MFCD09966063
Formula :	C₅H₅ClN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CTMIYYREUVYVEL-UHFFFAOYSA-N
M.W :	144.56	Pubchem ID :	11008039
Synonyms :

Calculated chemistry of [ 695-85-2 ]

Physicochemical Properties

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 :	0.0
Molar Refractivity :	33.53
TPSA :	35.01 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) :	-6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.68
Log Po/w (XLOGP3) :	1.14
Log Po/w (WLOGP) :	1.14
Log Po/w (MLOGP) :	-0.07
Log Po/w (SILICOS-IT) :	1.56
Consensus Log Po/w :	1.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.88
Solubility :	1.9 mg/ml ; 0.0131 mol/l
Class :	Very soluble
Log S (Ali) :	-1.47
Solubility :	4.91 mg/ml ; 0.0339 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.37
Solubility :	0.612 mg/ml ; 0.00424 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.74

Safety of [ 695-85-2 ]

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

Application In Synthesis of [ 695-85-2 ]

* 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 [ 695-85-2 ]
Downstream synthetic route of [ 695-85-2 ]

[ 695-85-2 ] Synthesis Path-Upstream 1~5

1
[ 695-85-2 ]
[ 695-86-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With ammonia In ethanol at 130℃; for 12 h; Autoclave	A suspension of 4-chloro-5-methoxypyrimidine (I-89) (40 g, 280 mmol) in NH3 (g)/EtOH (4 M, 2000 mL) was poured into an autoclave at room temperature and stirred at 130 °C for 12 hr. TLC (CH2CI2/MeOH = 10:1 ) showed the reaction was complete. The mixture was cooled to room temperature and concentrated in vacuo to give a residue, to which was added CH2CI2 (100 mL) and the resulting mixture was stirred at room temperature for 30 min. The resulting suspension was filtered to remove NH4CI salt, and the filtrate was concentrated in vacuo to give the crude product. The crude product was stirred in a mixed solvent of EtOAc/CH2CI2 (50 mL, 4:1 ) for 30 min, filtered and concentrated in vacuo to obtain 4-amino-5-methoxypyrimidine (I-90) (30 g, 87percent) as a yellow solid. 1H NMR (400 MHz, DMSO-c/6) 8 ppm 8.01 (s, 1 H), 7.81 (s, 1 H), 6.75 (br. s., 2 H), 3.81 (s, 3 H).

Reference： [1] Patent: WO2016/97918, 2016, A1, . Location in patent: Page/Page column 80
[2] Organic Process Research and Development, 2015, vol. 19, # 6, p. 639 - 645
[3] European Journal of Medicinal Chemistry, 2009, vol. 44, # 10, p. 4179 - 4191

2
[ 19646-07-2 ]
[ 695-85-2 ]

Yield	Reaction Conditions	Operation in experiment
32%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 3 h; Inert atmosphere	General procedure: PdCl₂(dppf), PdCl₂(tbpf) and (A.^caPhos)PdCl₂. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl₂(dppf) (27.0 mg, 0.033 mmol, 5.0 molpercent), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH₄ (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.

Reference： [1] Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 191 - 209

3
[ 695-87-4 ]
[ 695-85-2 ]

Yield	Reaction Conditions	Operation in experiment
58%	at 115℃; for 3 h;	A suspension of 1.9 g (0.015 mol) of 5-methoxy-3H-pyrimidin-4-one (Example P2) in 4.2 ml (0.046 mol) of phosphorus oxychloride and 5.0 mi (0.031 mol) of N, N-diethylaniline is heated at 115°C for 3 hours. The dark, homogeneous mixture obtained is hydrolyse by adding crushed ice, the temperature being kept below 30°C. Extraction with diethyl ether, drying of the combined organic ethereal phases over sodium sulfate, and purification on a silica gel column (eluant : ethyl acetate/n-hexane 1/9) yields the desired target compound in a yield of 1.3 g (58 percent of theory). Further purification by means of sublimation at 80-85°C/15 Torr yields the desired title compound, having a melting point of 63-64°C. oh NMR (300 MHz, Ceci3) : 8.635 ppm (s, 1H) ; 8.321 ppm (s, 1H) ; 4.025 ppm (s, 3H).

Reference： [1] European Journal of Medicinal Chemistry, 2009, vol. 44, # 10, p. 4179 - 4191
[2] Patent: WO2003/87067, 2003, A1, . Location in patent: Page/Page column 37

4
[ 695-87-4 ]
[ 695-85-2 ]

Yield	Reaction Conditions	Operation in experiment
58%	for 6 h; Reflux	A suspension of 5-methoxypyrimidin-4-ol (1-88) (57 g, 0.452 mol) in POCI3 (540 mL) was heated at reflux for 6 hr. TLC (CH2CI2/MeOH =10:1 ) showed the reaction was complete. Most of the POCI3 was removed under reduced pressure, and the residue was poured into ice-water (2 L), basified with K2C03 (250 g) to pH ~ 7. The mixture was then extracted with EtOAc BME (3:1 , 4 x 250 mL). The organic layers were combined, washed with brine (100 mL) and dried over Na2S04, filtered and concentrated in vacuo to give 4-chloro-5-methoxypyrimidine (I-89) (3S g, 58percent) as a yellow solid. 1H NMR (400 MHz, DMSO-c/6) 8 ppm 8.63 (s, 1 H), 8.32 (s, 1 H), 4.02 (s, 3 H).

Reference： [1] Journal of Organic Chemistry, 1997, vol. 62, # 26, p. 9192 - 9202
[2] Patent: WO2016/97918, 2016, A1, . Location in patent: Page/Page column 80
[3] Organic Process Research and Development, 2015, vol. 19, # 6, p. 639 - 645

5
[ 695-87-4 ]
[ 695-85-2 ]

Reference： [1] Patent: US5550239, 1996, A,

[ 695-85-2 ] Synthesis Path-Downstream 1~22

1
[ 120-43-4 ]
[ 695-85-2 ]
[ 1027025-80-4 ]