[ CAS No. 1194-21-4 ] {[proInfo.proName]}

Name: 1194-21-4|2-Amino-6-chloropyrimidin-4(3H)-one|97%
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Quality Control of [ 1194-21-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1194-21-4 ]

Product Details of [ 1194-21-4 ]

CAS No. :	1194-21-4	MDL No. :	MFCD12028107
Formula :	C₄H₄ClN₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VBWACOJLJYUFKJ-UHFFFAOYSA-N
M.W :	145.55	Pubchem ID :	135403356
Synonyms :

Calculated chemistry of [ 1194-21-4 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	34.27
TPSA :	71.77 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.38
Log Po/w (XLOGP3) :	-0.46
Log Po/w (WLOGP) :	0.01
Log Po/w (MLOGP) :	-0.17
Log Po/w (SILICOS-IT) :	1.14
Consensus Log Po/w :	0.18

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.95
Solubility :	16.5 mg/ml ; 0.113 mol/l
Class :	Very soluble
Log S (Ali) :	-0.58
Solubility :	38.2 mg/ml ; 0.262 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.79
Solubility :	2.34 mg/ml ; 0.0161 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 1194-21-4 ]

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 [ 1194-21-4 ]

* 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 [ 1194-21-4 ]
Downstream synthetic route of [ 1194-21-4 ]

[ 1194-21-4 ] Synthesis Path-Upstream 1~6

1
[ 1194-21-4 ]
[ 56-05-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2429 - 2439

2
[ 56-05-3 ]
[ 1194-21-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydroxide In water for 5 h; Reflux	To a solution of 4,6-dichloropyrimidin-2-amine (21.2 g, 129.27 mmol) in 200 mL of IN NaOH was added NaOH (4 g, 100.00 mmol) in several batches. The resulting solution was refluxed for 5 hours. The reaction mixture was cooled in a bath of H₂O/ice. Adjustment of the pH to 5-6 was accomplished by the addition of CH₃COOH. A filtration was performed and the filter cake was collected. The solid was washed with water and dried under an oven with reduced pressure. This resulted in 17 g (86percent) of 2-amino-6-chloropyrirnidin-4(3H)-one as a white solid.

Reference： [1] Chemistry (Weinheim an der Bergstrasse, Germany), 2002, vol. 8, # 1, p. 293 - 301
[2] Organic Letters, 2009, vol. 11, # 1, p. 61 - 64
[3] Patent: WO2009/139834, 2009, A1, . Location in patent: Page/Page column 93
[4] Journal of the Chemical Society, 1951, p. 3,6
[5] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 8, p. 1081 - 1083
[6] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 23, p. 6610 - 6614
[7] Patent: WO2004/56831, 2004, A1, . Location in patent: Page 74-75

3
[ 1193-21-1 ]
[ 1194-21-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With acetic acid In sodium hydroxide	EXAMPLE 3 2-Amino-6-chloro-4(3H)-pyrimidinone A suspension of 250 g (0.1525 mole) of 2-amino, 4,6-dichloropyrimidine in 500 ml of 1N NaOH was heated to reflux. The solids gradually dissolved, and a complete solution formed after 4-5 hours. Acidification with about 70 ml of acetic acid gave a pH of 4 and precipitated a voluminous white solid that was filtered and washed with three 50-ml volumes of water. After drying in a vacuum over at 80° C./20 mm Hg, 21.75 g of product was obtained as fluffy white crystals, m.p. 260°-261° C., yield 99percent. NMR, IR and MS were consistent with the expected compound. Analysis: Calculated for: C₄ H₄ N₃ OCl: C, 32.37; H, 2.93. Found: C, 32.75; H, 2.81.

Reference： [1] Patent: US4939252, 1990, A,

4
[ 56-09-7 ]
[ 1194-21-4 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 6, p. 1537 - 1539

5
[ 5734-64-5 ]
[ 1194-21-4 ]

Reference： [1] Journal of the Chemical Society, 1951, p. 1497,1499

6
[ 1194-21-4 ]
[ 1007-99-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sulfuric acid; nitric acid In water at 20℃;	To a solution of 2-amino-6-chloropyrimidin-4(3H)-one (10 g, 68.73 mmol) in H₂SO4 (46 mL, 98percent) at 4O⁰C was added HNO₃ (9 g, 65percent) dropwise with stirring. The resulting solution was stirred for an hour at room temperature. The solution was poured into 100 g of ice. A filtration was performed. The filter cake was collected and dried under an oven with reduced pressure, resulted in 12 g (87percent) of 2-amino-6-chloro-5-nitropyrimidin-4(3H)-one as a yellow solid. ¹H NMR (300 MHz, DMSO-d6) δ 7.13(1H, s), 8.59 (IH, s), 12.16 (IH, s).

Reference： [1] Chemistry (Weinheim an der Bergstrasse, Germany), 2002, vol. 8, # 1, p. 293 - 301
[2] Patent: US4939252, 1990, A,
[3] Patent: WO2009/139834, 2009, A1, . Location in patent: Page/Page column 93-94
[4] Journal of Heterocyclic Chemistry, 1985, vol. 22, # 4, p. 1035 - 1040
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 1645 - 1660
[6] Tetrahedron Letters, 2001, vol. 42, # 9, p. 1793 - 1795
[7] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 8, p. 1081 - 1083
[8] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 23, p. 6610 - 6614
[9] Tetrahedron Letters, 2009, vol. 50, # 44, p. 6022 - 6024

[ 1194-21-4 ] Synthesis Path-Downstream 1~74

1
[ 56-05-3 ]
[ 1194-21-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydroxide; In water; for 5h;Reflux;	To a solution of 4,6-dichloropyrimidin-2-amine (21.2 g, 129.27 mmol) in 200 mL of IN NaOH was added NaOH (4 g, 100.00 mmol) in several batches. The resulting solution was refluxed for 5 hours. The reaction mixture was cooled in a bath of H2O/ice. Adjustment of the pH to 5-6 was accomplished by the addition of CH3COOH. A filtration was performed and the filter cake was collected. The solid was washed with water and dried under an oven with reduced pressure. This resulted in 17 g (86percent) of 2-amino-6-chloropyrirnidin-4(3H)-one as a white solid.
	With sodium hydroxide; water; for 5h;Heating / reflux;	2-Amino-4, 6-dichloropyrimidine (10.6 g) was suspended in 1N NAOH (100 mL) and heated to reflux. Additional NaOH(s) (1.0 g) was added after 2 h and 4 h. After 5H, the solution was cooled with an ice bath and neutralized with acetic acid. The white precipitate was filtered, washed with water, and dried on a high vacuum to yield 9.28 g of white solid.

Reference： [1]Chemistry - A European Journal,2002,vol. 8,p. 293 - 301
[2]Organic Letters,2009,vol. 11,p. 61 - 64
[3]Patent: WO2009/139834,2009,A1 .Location in patent: Page/Page column 93
[4]Journal of the Chemical Society,1951,p. 3,6
[5]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1081 - 1083
[6]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6610 - 6614
[7]Patent: WO2004/56831,2004,A1 .Location in patent: Page 74-75

2
[ 1194-21-4 ]
[ 100-34-5 ]
2-amino-6-chloro-pyrimidine-4,5-dione-5-phenylhydrazone [ No CAS ]

Reference： [1]Journal of the Chemical Society,1951,p. 1497,1499

3
[ 1194-21-4 ]
[ 75-04-7 ]
[ 164525-11-5 ]

Reference： [1]Journal of the Chemical Society,1951,p. 3,6
[2]Journal of Medicinal Chemistry,1985,vol. 28,p. 1870 - 1874
[3]Journal of medicinal chemistry,1993,vol. 36,p. 3431 - 3436

4
[ 1194-21-4 ]
[ 141-43-5 ]
[ 1077-04-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1998,p. 3025 - 3031
[2]Journal of the American Chemical Society,1953,vol. 75,p. 4311,4313

5
[ 1194-21-4 ]
[ 74-89-5 ]
[ 54004-20-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	In water; at 120 - 130℃; for 8h;	Preparation of Intermediate N-lTo a solution of Intermediate M (5g, 34.48 mmol) was added 40percent aqueous methyl amine solution (50 mL), and the resulting mixture was heated in a steel bomb at 120-130 °C (bath temperature) for 8 hours. The reaction mixture was cooled to room temperature and then concentrated to obtain a crude residue that was washed with EtOH several times to obtain pure Intermediate N-l (3.5g, 72percent). Rf = 0.6 (20percent MeOH/CHCl3/0.2 mL of aqueous NH3). 1H-NMR (400MHz, DMSO-d6) delta 9.66 (br. s, exchanged with D20, 1H), 6.25 (br. s, exchanged with D20, 1H), 6.10 (br. s, exchanged with D20, 2H), 4.36 (s, exchanged with D20, 1H), 2.61(s, 3H). Mass (APCI positive mode, m/z): 141.0 (M++l).

Reference： [1]Patent: WO2011/35009,2011,A1 .Location in patent: Page/Page column 53
[2]Journal of the Chemical Society,1957,p. 4157,4160

8
[ 5734-64-5 ]
[ 1194-21-4 ]

Reference： [1]Journal of the Chemical Society,1951,p. 1497,1499

9
[ 110-91-8 ]
[ 1194-21-4 ]
[ 37409-97-5 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1972,vol. 759,p. 76 - 83

10
[ 107-10-8 ]
[ 1194-21-4 ]
[ 90000-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 120 - 130℃; for 8h;	Synthesis of Compound (50)To a solution of Intermediate M (5g, 34.48 mmol) was added n-propylamine (50 mL) and H20 (20 mL), and the resulting mixture was heated in a steel bomb at 120-130 °C (bath temperature) for 8 hours. The reaction mixture was cooled to room temperature and concentrated to obtain a crude residue. This residue was washed with EtOH several times to obtain pure Compound (50) as a yellow solid. Rf = 0.5(20percent MeOH/CHC /0.2 mL of aqueous NH3). - MR (400MHz, DMSO-<3/4) delta 9.62 (s, exchanged with D20, 1H), 6.35 (s, exchanged with D20, 1H), 6.10 (s, exchanged with D20, 1H), 4.49 (s, 1H), 3.34 (br. s, 2H), 1.70-1.60 (m, 2H), 0.85 (t, J = 7.6 Hz, 2H). Mass (m/z): 168.8 (M++l). HPLC: (Column: Acquity; UPLC BEH; C-8 (100 chi 2.1 mm) 1.7 mu, A: 0.05M Ammonium bicarbonate (Aqueous), B: Acetonitrile, T/percentB: 0/20, 4/80, 6/80, 6.1/20, Flow rate: 0.3 mL/min, Diluent: A:B (7:3)), Rt=1.194 min, 98.07 (215 nra), 98.51 (254 nra), 96.45 (Max plot).

Reference： [1]Chemical Communications,2009,p. 668 - 670
[2]Journal of medicinal chemistry,1993,vol. 36,p. 3431 - 3436
[3]Patent: WO2011/35009,2011,A1 .Location in patent: Page/Page column 57

11
[ 1194-21-4 ]
[ 111-86-4 ]
2-Amino-6-octylamino-3H-pyrimidin-4-one [ No CAS ]

Reference： [1]Journal of medicinal chemistry,1993,vol. 36,p. 3431 - 3436

12
[ 1194-21-4 ]
[ 111-26-2 ]
[ 146203-12-5 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 1024 - 1031
[2]Journal of medicinal chemistry,1993,vol. 36,p. 3431 - 3436

13
[ 1194-21-4 ]
[ 111-68-2 ]
2-Amino-6-heptylamino-3H-pyrimidin-4-one [ No CAS ]

Reference： [1]Journal of medicinal chemistry,1993,vol. 36,p. 3431 - 3436

14
[ 1194-21-4 ]
[ 4048-33-3 ]
2-Amino-6-(6-hydroxy-hexylamino)-3H-pyrimidin-4-one [ No CAS ]

Reference： [1]Journal of medicinal chemistry,1993,vol. 36,p. 3431 - 3436

15
[ 1194-21-4 ]
[ 2432-74-8 ]
6-(2-Amino-6-oxo-1,6-dihydro-pyrimidin-4-ylamino)-hexanenitrile [ No CAS ]

Reference： [1]Journal of medicinal chemistry,1993,vol. 36,p. 3431 - 3436

16
[ 1194-21-4 ]
[ 2038-57-5 ]
[ 98510-50-0 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1870 - 1874

17
[ 1194-21-4 ]
[ 118-31-0 ]
2-amino-4-<(naphthylmethyl)amino>pyrimidin-6-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 1024 - 1031

18
[ 1194-21-4 ]
[ 17734-22-4 ]
2-Amino-6-(7-phenyl-heptylamino)-3H-pyrimidin-4-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1870 - 1874

19
[ 1194-21-4 ]
[ 108-91-8 ]
[ 60462-36-4 ]

Reference： [1]Journal of medicinal chemistry,1993,vol. 36,p. 3431 - 3436

20
[ 1194-21-4 ]
[ 106-49-0 ]
[ 57628-56-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1537 - 1539

21
[ 1194-21-4 ]
[ 110-58-7 ]
2-Amino-6-pentylamino-3H-pyrimidin-4-one [ No CAS ]

Reference： [1]Journal of medicinal chemistry,1993,vol. 36,p. 3431 - 3436

22
[ 1194-21-4 ]
[ 64-04-0 ]
[ 100890-98-0 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1870 - 1874

23
[ 1194-21-4 ]
[ 75-31-0 ]
[ 164525-12-6 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1870 - 1874

24
[ 1194-21-4 ]
[ 109-73-9 ]
[ 60462-37-5 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 12860 - 12861
[2]Journal of medicinal chemistry,1993,vol. 36,p. 3431 - 3436

25
[ 1194-21-4 ]
[ 109-73-9 ]
[ 5457-91-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1537 - 1539

26
[ 1194-21-4 ]
[ 100-63-0 ]
[ 80082-11-7 ]
[ 80082-33-3 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 674 - 680
[2]Journal of Organic Chemistry,1982,vol. 47,p. 674 - 680

27
[ 1194-21-4 ]
[ 103-67-3 ]
[ 37409-94-2 ]

Reference： [1]Journal of Organic Chemistry,1985,vol. 50,p. 2474 - 2480

29
[ 1194-21-4 ]
[ 3218-02-8 ]
[ 146203-13-6 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 61 - 64
[2]Journal of Medicinal Chemistry,1993,vol. 36,p. 1024 - 1031

30
[ 1194-21-4 ]
[ 45467-35-4 ]
6-<<<(E)-2-(hydroxymethyl)cyclopropyl>methyl>amino>isocytosine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2304 - 2315

31
[ 1194-21-4 ]
[ 116663-92-4 ]
[ 116663-93-5 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2304 - 2315

32
[ 1194-21-4 ]
[ 156-87-6 ]
2-Amino-6-(3-hydroxy-propylamino)-3H-pyrimidin-4-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1870 - 1874

33
[ 1194-21-4 ]
[ 100-46-9 ]
[ 60308-49-8 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1870 - 1874

34
[ 1194-21-4 ]
[ 60-32-2 ]
[ 1026679-80-0 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 1024 - 1031

35
[ 1194-21-4 ]
[ 1007-99-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sulfuric acid; nitric acid;	EXAMPLE 4 2-Amino-6-chloro-5-nitro-4(3H)-pyrimidinone A solution of 64 ml of concentrated sulfuric acid and 64 ml of concentrated nitric acid was cooled to 0° to -5° C. in an ice-salt bath, when 11.75 g (0.0807 mole) of 2-amino-6-chloro-4-(3H)-pyrimidinone were added in small portions so that the reaction temperature did not exceed 10° C. After 45 minutes, all of the starting material was added. The mixture was stirred for 3 hours at 5° C., when the mixture was poured over 400 g of ice and stirred for 1 hour at 5° C. The precipitated solids were collected by filtration and washed with 35 ml of ethanol and 35 ml of ether and dried at 20° C./2 mm Hg overnight to produce 14.7 g of a yellow solid, m.p. 268° C. The yield was 87percent. NMR, IR and MS were consistent with the expected compound. Analysis: Calculated for C4 H3 ClN4 O3.H2 O: C, 23.04; H, 2.42; N, 26.87; H2 O 8.64. Found: C, 22.70; H, 2.32; N, 26.82; H2 O (Karl Fischer), 8.48.
87%	With sulfuric acid; nitric acid; In water; at 20℃;	To a solution of 2-amino-6-chloropyrimidin-4(3H)-one (10 g, 68.73 mmol) in H2SO4 (46 mL, 98percent) at 4O0C was added HNO3 (9 g, 65percent) dropwise with stirring. The resulting solution was stirred for an hour at room temperature. The solution was poured into 100 g of ice. A filtration was performed. The filter cake was collected and dried under an oven with reduced pressure, resulted in 12 g (87percent) of 2-amino-6-chloro-5-nitropyrimidin-4(3H)-one as a yellow solid. 1H NMR (300 MHz, DMSO-d6) delta 7.13(1H, s), 8.59 (IH, s), 12.16 (IH, s).

Reference： [1]Chemistry - A European Journal,2002,vol. 8,p. 293 - 301
[2]Patent: US4939252,1990,A
[3]Patent: WO2009/139834,2009,A1 .Location in patent: Page/Page column 93-94
[4]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1035 - 1040
[5]Journal of the Chemical Society. Perkin transactions I,1985,p. 1645 - 1660
[6]Tetrahedron Letters,2001,vol. 42,p. 1793 - 1795
[7]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1081 - 1083
[8]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6610 - 6614
[9]Tetrahedron Letters,2009,vol. 50,p. 6022 - 6024

36
[ 56-09-7 ]
[ 1194-21-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1537 - 1539

37
[ 1194-21-4 ]
[ 367-21-5 ]
3-chloro-4-fluoroaniline hydrochloride [ No CAS ]
2-Amino-6-(3-chloro-4-fluoro-phenylamino)-3H-pyrimidin-4-one [ No CAS ]