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[ CAS No. 73-40-5 ]

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Chemical Structure| 73-40-5
Chemical Structure| 73-40-5
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CAS No. :73-40-5 MDL No. :MFCD00071533
Formula : C5H5N5O Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :151.13 g/mol Pubchem ID :135398634
Synonyms :

1. Guanine

Safety of [ 73-40-5 ]

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 [ 73-40-5 ]

  • Upstream synthesis route of [ 73-40-5 ]
  • Downstream synthetic route of [ 73-40-5 ]

[ 73-40-5 ] Synthesis Path-Upstream   1~27

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Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 1998, # 6, p. 1365 - 1374
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Patent: US2697709, 1952, ,
[2] Journal of the American Chemical Society, 1955, vol. 77, p. 1676
[3] Patent: US2884667, 1955, ,
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  • [ 39639-47-9 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2011, vol. 30, # 7-8, p. 503 - 511
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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YieldReaction ConditionsOperation in experiment
55% With trichlorophosphate In ammonium hydroxide; water; N,N-dimethyl-formamide EXAMPLE 1
46.0 g (0.3 mol) of phosphorus oxychloride was added to 73.1 g (1.0 mol) of N,N-dimethylformamide, and 15.1 g (0.1 mol) of guanine (manufactured by Sumika Fine Chemicals Co., Ltd.) was then added, followed by stirring at 100° C. for 4 hours.
After cooling, 100 ml of water was carefully added at 20° C.
After stirring at room temperature for 24 hours, the precipitating crystal was collected by filtration and dissolved in 100 ml of 25percent aqueous ammonia with heating, and the insoluble substances were filtered out.
The mother liquor was concentrated under reduced pressure, and the precipitating crystal was collected by filtration to yield 9.3 g (0.055 mol) of a white crystal of 2-amino-6-chloropurine (yield 55percent).
42% With tetraethylammonium chloride; trichlorophosphate In water; acetonitrile EXAMPLE 1
2-Amino-6-chloropurine (Method A)
A mixture of guanine (4.5g, 30 mmol), tetraethylammonium chloride (7.46 g, 45 mmol monohydrate, pre-dried), phosphorus oxychloride (16.5 ml) and acetonitrile (60 ml) was heated under reflux for 70 minutes and allowed to cool.
The solid material was filtered off and suspended in water.
The aqueous mixture was brought to alkaline pH with aqueous sodium hydroxide and back to pH 7 with dilute hydrochloric acid.
Continuous extraction (24 hours) with ethyl acetate afforded 2-amino-6-chloropurine as a white solid (2.12 g, 42percent).
42% With tetraethylammonium chloride; trichlorophosphate In water; acetonitrile Example 1
2-Amino-6-chloropurine (Method A)
A mixture of guanine (4.5g, 30mmol), tetraethylammonium chloride (7.46g, 45mmol monohydrate, pre-dried), phosphorus oxychloride (16.5ml) and acetonitrile (60ml) was heated under reflux for 70 minutes and allowed to cool.
The solid material was filtered off and suspended in water.
The aqueous mixture was brought to alkaline pH with aqueous sodium hydroxide and back to pH 7 with dilute hydrochloric acid.
Continuous extraction (24 hours) with ethyl acetate afforded 2-amino-6-chloropurine as a white solid (2.12g, 42percent).
30% With tetraethylammonium chloride; trichlorophosphate In water; acetonitrile EXAMPLE 2
2-Amino-6-chloropurine (Method B)
A mixture of guanine (4.5 g, 30 mmol), tetraethylammonium chloride (30 mmol), phosphorus oxychloride (16.5 ml and acetonitrile (60 ml) was placed in a flask in an ultrasonic bath at 60° C. for 2 hours.
The mixture was then heated under reflux for 90 minutes and allowed to cool.
The solid material was filtered off and suspended in water.
The aqueous mixture was brought to alkaline pH with aqueous sodium hydroxide and back to pH 7 with dilute hydrochloric acid.
Continuous extraction with ethyl acetate afforded 2-amino-6-chloropurine as a white solid (1.55 g, 30percent).
30% With tetraethylammonium chloride; trichlorophosphate In water; acetonitrile Example 2
2-Amino-6-chloropurine (Method B)
A mixture of guanine (4.5g, 30mmol), tetraethylammonium chloride (30mmol), phosphorus oxychloride (16.5ml and acetonitrile (60ml) was placed in a flask in an ultrasonic bath at 60oC for 2 hours.
The mixture was then heated under reflux for 90 minutes and allowed to cool.
The solid material was filtered off and suspended in water.
The aqueous mixture was brought to alkaline pH with aqueous sodium hydroxide and back to pH 7 with dilute hydrochloric acid.
Continuous extraction with ethyl acetate afforded 2-amino-6-chloropurine as a white solid (1.55g, 30percent).

Reference: [1] Heterocycles, 2008, vol. 75, # 11, p. 2803 - 2808
[2] Patent: US5389637, 1995, A,
[3] Patent: US4736029, 1988, A,
[4] Patent: EP203685, 1991, B1,
[5] Patent: US4736029, 1988, A,
[6] Patent: EP203685, 1991, B1,
[7] Nucleosides, Nucleotides and Nucleic Acids, 2011, vol. 30, # 7-8, p. 503 - 511
[8] Bulletin of the Chemical Society of Ethiopia, 2010, vol. 24, # 3, p. 425 - 432
[9] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 675 - 686
[10] Patent: CN106336443, 2017, A, . Location in patent: Paragraph 0063; 0064
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YieldReaction ConditionsOperation in experiment
54% With trichlorophosphate In water; acetone; acetonitrile EXAMPLE 1
(2-Amino-6-chloropurine)
A mixture of guanine (22.7 g, 0.15 mol), methyltriethylammonium chloride (TEMAC) (45.5 g, 0.3 mol), phosphorus oxychloride (82.6 ml, 0.9 mol) and acetonitrile (67 ml) was heated at 60° C. with stirring for 6 hours and then cooled to 10° C.
The solid material was filtered off and suspended in water (300 mls).
The aqueous mixture was brought to alkaline pH with aqueous sodium hydroxide to achieve dissolution and powdered carbon (6.8 g) added.
The mixture was stirred for 1 hour and then filtered to remove the carbon.
Acetone (72 mls) was added and then the pH reduced to 7 with dilute hydrochloric acid.
The product was filtered off, washed with acetone/water (50:50 mixture, 50 mls), water (50 mls), acetone/water (50:50 mixture, 50 mls) and acetone (50 mls) and then dried to give 2-amino-6-chloropurine as a cream coloured solid (14.77 g, 54 percent yield).
Reference: [1] Patent: US5910589, 1999, A,
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Reference: [1] Patent: US5663338, 1997, A,
[2] Patent: US5663338, 1997, A,
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  • [ 10310-21-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 5, p. 1140 - 1144
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  • [ 5451-40-1 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2011, vol. 30, # 7-8, p. 503 - 511
[2] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 675 - 686
[3] European Journal of Organic Chemistry, 2018, vol. 2018, # 41, p. 5763 - 5772
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  • [ 5451-40-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 5, p. 1140 - 1144
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  • [ 19916-73-5 ]
Reference: [1] Bulletin of the Chemical Society of Ethiopia, 2010, vol. 24, # 3, p. 425 - 432
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  • [ 19962-37-9 ]
YieldReaction ConditionsOperation in experiment
72.7% With acetic anhydride In ethanol; N,N-dimethyl acetamide EXAMPLE 52
Preparation of N2 -Acetylguanine
Guanine (10.1 g) was suspended in N,N-dimethylacetamide (100 ml), and acetic anhydride (20 ml) was added thereto.
The mixture was stirred under reflux for 2 hours and filtered hot.
After cooling the filtrate to room temperature, the solid precipitated was filtered, and the solid suspended in ethanol (66 ml).
After stirring 1.5 hours, the suspension was filtered.
The solid thus obtained was stirred under reflux in 50percent ethanol for 3 hours, and the solution cooled.
The solid product thus obtained was filtered, washed with 50percent ethanol, and dried to provide the desired product (9.36 g, 72.7percent) as white solid.
1 H NMR (DMSO-d6) δ 13.14(bd,1H), 12.14(bs,1H), 11.67(bs,1H), 8.10 (bs,1H), 2.28(s,3H)
Reference: [1] Patent: US6034087, 2000, A,
[2] Organic Letters, 2015, vol. 17, # 20, p. 4933 - 4935
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Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1987, vol. 41, # 8, p. 564 - 568
[2] Synthesis, 2004, # 12, p. 2026 - 2034
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1920 - 1923
[4] Angewandte Chemie - International Edition, 2010, vol. 49, # 11, p. 1963 - 1966
[5] Chemical Communications, 2010, vol. 46, # 8, p. 1218 - 1220
[6] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8915 - 8930
[7] Bioconjugate Chemistry, 2017, vol. 28, # 7, p. 1893 - 1905
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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  • [ 82410-32-0 ]
Reference: [1] Patent: US4508898, 1985, A,
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  • [ 82410-32-0 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2003, vol. 46, p. S221 - S221
[2] Synthetic Communications, 2004, vol. 34, # 5, p. 917 - 932
[3] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 22, p. 3933 - 3938
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 3, p. 651 - 654
[5] Helvetica Chimica Acta, 1989, vol. 72, # 7, p. 1495 - 1500
[6] Canadian Journal of Chemistry, 1982, vol. 60, # 24, p. 3005 - 3010
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Reference: [1] Patent: EP187297, 1991, B1,
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Reference: [1] Synthesis, 2004, # 12, p. 2026 - 2034
[2] Tetrahedron, 1999, vol. 55, # 16, p. 5239 - 5252
[3] Tetrahedron, 1999, vol. 55, # 16, p. 5239 - 5252
[4] Heterocycles, 2008, vol. 75, # 11, p. 2803 - 2808
  • 26
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  • [ 79-30-1 ]
  • [ 21047-89-2 ]
Reference: [1] Tetrahedron, 1995, vol. 51, # 44, p. 12069 - 12082
[2] Magnetic Resonance in Chemistry, 2013, vol. 51, # 1, p. 60 - 64
[3] Patent: US6075143, 2000, A,
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  • [ 21047-89-2 ]
Reference: [1] Heterocycles, 2007, vol. 71, # 12, p. 2659 - 2668
[2] Journal of Organic Chemistry, 2011, vol. 76, # 14, p. 5574 - 5583
[3] Journal of the American Chemical Society, 2017, vol. 139, # 25, p. 8537 - 8546
[4] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 1, p. 19 - 26
[5] Journal of Organic Chemistry, 2010, vol. 75, # 22, p. 7932 - 7935
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