[ CAS No. 73576-33-7 ] {[proInfo.proName]}

Name: 73576-33-7|4-Chloro-6-isopropylpyrimidin-2-amine|98%
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SKU: A257710
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Quality Control of [ 73576-33-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 73576-33-7 ]

Product Details of [ 73576-33-7 ]

CAS No. :	73576-33-7	MDL No. :	MFCD03840198
Formula :	C₇H₁₀ClN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SPMMDFHRMVXLLO-UHFFFAOYSA-N
M.W :	171.63	Pubchem ID :	2773619
Synonyms :

Calculated chemistry of [ 73576-33-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.43
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.03
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) :	-5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	1.98
Log Po/w (WLOGP) :	1.84
Log Po/w (MLOGP) :	1.02
Log Po/w (SILICOS-IT) :	1.69
Consensus Log Po/w :	1.68

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.49
Solubility :	0.556 mg/ml ; 0.00324 mol/l
Class :	Soluble
Log S (Ali) :	-2.69
Solubility :	0.347 mg/ml ; 0.00202 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.73
Solubility :	0.322 mg/ml ; 0.00187 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 73576-33-7 ]

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

Application In Synthesis of [ 73576-33-7 ]

* 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 [ 73576-33-7 ]
Downstream synthetic route of [ 73576-33-7 ]

[ 73576-33-7 ] Synthesis Path-Upstream 1~1

1
[ 7152-15-0 ]
[ 73576-33-7 ]

Reference： [1] Journal of Medicinal Chemistry, 1980, vol. 23, # 5, p. 535 - 541
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2429 - 2439
[3] Patent: WO2018/39621, 2018, A1,

[ 73576-33-7 ] Synthesis Path-Downstream 1~61

1
[ 73576-33-7 ]
[ 73576-42-8 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 535 - 541

2
2-amino-6-isopropyl-4(3H)-pyrimidinone [ No CAS ]
[ 73576-33-7 ]

Yield	Reaction Conditions	Operation in experiment
51%	With trichlorophosphate; for 4.0h;Heating;	2-Amino-6-isopropylpyrimidin-4(5H)-one (180) (3.7 g, 24.0 mmol) was treated with phosphoryl chloride (16 mL) and this mixture heated for 4 hours. The homogeneous mixture was cooled and poured onto ice. This temperature was maintained while adding water (500 mL) and adjustment of the pH to 7. The aqueous layer was extracted with ethyl acetate (3X) and the organics washed with brine. Drying over sodium sulfate, filtration and evaporation of the solvent yielded a solid that was chromatographed in 0-25% ethyl acetate in hexanes. The purified material was crystallized from dichloromethane in hexanes to afford the title product (181) (2.1 g, 51%). This material was used directly in the next step.

Reference： [1]Patent: WO2018/39621,2018,A1 .Location in patent: Paragraph 00529-00530
[2]Journal of Medicinal Chemistry,1980,vol. 23,p. 535 - 541

3
[ 73576-33-7 ]
[ 124-40-3 ]
6-Isopropyl-N⁴,N⁴-dimethyl-pyrimidine-2,4-diamine [ No CAS ]

Reference： [1]Organic Magnetic Resonance,1982,vol. 20,p. 274 - 275

4
[ 109-01-3 ]
[ 73576-33-7 ]
4-isopropyl-6-(4-methyl-piperazin-1-yl)-pyrimidin-2-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In ethanol; at 150℃; for 0.166667h;Microwave irradiation;	Example 21; Synthesis of 4-/sopropyl-6-(4-methylpiperazin-1 -vDpyrimidin-2-amine (Compound 163); A solution of 4-chloro-6-/sopropylpyrimidin-2-amine (CAS RN73576-33-7) (32mg) and N-methylpiperazine (19mg) in ethanol (0.75ml) is heated to 15O0C for 10 mins in a microwave. The solution is concentrated in vacuo and partitioned between dichloromethane and 10% potassium carbonate solution. The EtOAc solution is dried over MgSOphi filtered, and concentrated in vacuo to afford the title compound as a yellow oil(45mg 100%). LCMS 236 [M+H]+, RT 1.72 mins (pH 5.8). 1H NMR 300 MHz (CDCI3) (delta ppm): 5.8 (1 H, s), 4.9 (2H, br s), 3.6 (4H, m), 2.7 (1 H, m), 2.45 (4H, m), 2.35 (3H, s), 1.2 (6H, d).

Reference： [1]Patent: WO2008/31556,2008,A2 .Location in patent: Page/Page column 146

5
[ 73576-33-7 ]
[ 73576-15-5 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 535 - 541

6
[ 73576-33-7 ]
[ 73576-26-8 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 535 - 541

7
[ 7152-15-0 ]
[ 73576-33-7 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 535 - 541
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 2429 - 2439
[3]Patent: WO2018/39621,2018,A1

9
[ 843663-18-3 ]
[ 73576-33-7 ]
[ 1271021-99-8 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1871 - 1895

10
[ 843663-18-3 ]
[ 73576-33-7 ]
[ 1271021-75-0 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1871 - 1895

11
2-amino-6-isopropylpyrimidin-4-ol [ No CAS ]
[ 73576-33-7 ]

Yield	Reaction Conditions	Operation in experiment
89%	With trichlorophosphate; at 100℃; for 1.0h;	(Into a 20 mL round-bottom flask was placed 2-amino-6-(propan-2-yl)pyrimidin-4-ol (300 mg, 1.96 mmol, 1.00 equiv), POCb (5 mL). The resulting solution was stirred for 1 h at 100 C. The resulting mixture was (0942) concentrated under vacuum.. This resulted in 300 mg (89%) of the title compound as light brown oil, Analytical Data: LC-MS: (ES, m/z): R.T::::1 042 mm. mz ::::172 [M±1].

Reference： [1]Patent: WO2019/79485,2019,A1 .Location in patent: Paragraph 0568
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 2429 - 2439

12
[ 73576-33-7 ]
[ 1046447-88-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2429 - 2439

13
[ 122536-77-0 ]
[ 73576-33-7 ]
C₁₆H₂₇N₅O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2429 - 2439

14
[ 73576-33-7 ]
[ 392338-15-7 ]
C₁₇H₂₉N₅O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2429 - 2439

15
[ 201230-82-2 ]
[ 73576-33-7 ]
2-amino-N-(4-chloro-6-isopropylpyrimidin-2-yl)-6-isopropylpyrimidine-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%	With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; under 22502.3 Torr; for 3.0h;Inert atmosphere; Autoclave;	General procedure: 2-Amino-4-chloro-6-isopropylpyrimidine (3, 1.0 mmol,171.6 mg) or 143.6 mg 2-amino-4-chloro-6-methylpyrimidine(4, 1 mmol), 62.8 mg iodoferrocene (1, 0.2 mmol),3.4 mg Pd(OAc)2 (0.01 mmol), 5.4 mg PPh3 (0.02 mmol),146 mm3 triethylamine (1.0 mmol), and 4 cm3 DMF weretransferred under an inert atmosphere into a stainless steelautoclave. It was charged with carbon monoxide (30 bar atroom temperature) and stirred at 100 C for 3 h. Theproducts were isolated by column chromatography (silica,eluent: n-hexane/EtOAc = 1/1).

Reference： [1]Monatshefte fur Chemie,2014,vol. 145,p. 1981 - 1986

16
[ 201230-82-2 ]
N-(4-chloro-6-isopropylpyrimidin-2-yl)-ferrocenecarboxamide [ No CAS ]
[ 73576-33-7 ]
N-(4-chloro-6-isopropylpyrimidin-2-yl)-2-(ferrocenoylamino)-6-isopropylpyrimidine-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; under 22502.3 Torr; for 3.0h;Inert atmosphere; Autoclave;	General procedure: 2-Amino-4-chloro-6-isopropylpyrimidine (3, 1.0 mmol,171.6 mg) or 143.6 mg 2-amino-4-chloro-6-methylpyrimidine(4, 1 mmol), 62.8 mg iodoferrocene (1, 0.2 mmol),3.4 mg Pd(OAc)2 (0.01 mmol), 5.4 mg PPh3 (0.02 mmol),146 mm3 triethylamine (1.0 mmol), and 4 cm3 DMF weretransferred under an inert atmosphere into a stainless steelautoclave. It was charged with carbon monoxide (30 bar atroom temperature) and stirred at 100 C for 3 h. Theproducts were isolated by column chromatography (silica,eluent: n-hexane/EtOAc = 1/1).

Reference： [1]Monatshefte fur Chemie,2014,vol. 145,p. 1981 - 1986

17
[ 1273-76-3 ]
[ 201230-82-2 ]
[ 73576-33-7 ]
N-(4-chloro-6-isopropylpyrimidin-2-yl)-ferrocenecarboxamide [ No CAS ]
N-(4-chloro-6-isopropylpyrimidin-2-yl)-2-(ferrocenoylamino)-6-isopropylpyrimidine-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; under 22502.3 Torr; for 3.0h;Inert atmosphere; Autoclave;	General procedure: 2-Amino-4-chloro-6-isopropylpyrimidine (3, 1.0 mmol,171.6 mg) or 143.6 mg 2-amino-4-chloro-6-methylpyrimidine(4, 1 mmol), 62.8 mg iodoferrocene (1, 0.2 mmol),3.4 mg Pd(OAc)2 (0.01 mmol), 5.4 mg PPh3 (0.02 mmol),146 mm3 triethylamine (1.0 mmol), and 4 cm3 DMF weretransferred under an inert atmosphere into a stainless steelautoclave. It was charged with carbon monoxide (30 bar atroom temperature) and stirred at 100 C for 3 h. Theproducts were isolated by column chromatography (silica,eluent: n-hexane/EtOAc = 1/1).

Reference： [1]Monatshefte fur Chemie,2014,vol. 145,p. 1981 - 1986

18
[ 73576-33-7 ]
[ 102-36-3 ]
1-(4-chloro-6-isopropylpyrimidin-2-yl)-3-(3,4-dichlorophenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In toluene; at 100℃; for 3.0h;	A mixture of <strong>[73576-33-7]4-chloro-6-isopropylpyrimidin-2-amine</strong> (0.70 g, 3.78 mmol) and 3,4- dichlorophenyl-isocyanate (0.77 g, 3.78 mmol) in toluene (5 mL) was heated to 100C for 3h. The precipitate formed was collected through filtration, and washed with ether/hexanes (1:1) to give the title compound (182) as a white solid (1.38, 94%). LC/MS: Rt = 5.06 min, m/z = 359.1, 361.1 [MH+]. This material was used directly in the next step.

Reference： [1]Patent: WO2018/39621,2018,A1 .Location in patent: Paragraph 00531-00532

19
[ 73576-33-7 ]
1-(3,4-dichlorophenyl)-3-(4-isopropyl-6-((3-(methylamino)propyl)amino)pyrimidin-2-yl)urea [ No CAS ]