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Quality Control of N,9-Diacetylguanine Purity: 96% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Details of N,9-Diacetylguanine

CAS No. :	3056-33-5
Formula :	C₉H₉N₅O₃
M.W :	235.20
SMILES Code :	CC(=O)NC1=NC2=C(N=CN2C(C)=O)C(=O)N1
Synonyms :	N,9-Diacetylguanine
MDL No. :	MFCD00142116
InChI Key :	GILZZWCROUGLIS-UHFFFAOYSA-N
Pubchem ID :	135433594

Safety of N,9-Diacetylguanine

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Application In Synthesis of N,9-Diacetylguanine

* 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.

Downstream synthetic route of [ 3056-33-5 ]

[ 3056-33-5 ] Synthesis Path-Downstream 1~35

1
[ 73-40-5 ]
[ 108-24-7 ]
[ 137226-08-5 ]
[ 3056-33-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 1153 - 1157.

2
[ 73-40-5 ]
[ 108-24-7 ]
[ 3056-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	In 1-methyl-pyrrolidin-2-one; at 20 - 150℃; for 27h;	[0100] A suspension of (5 g, 33 mmol) of guanine in 100 N-methy-2-pyrrolidinone NMP) and 20 ml acetic anhydride was heated to 150 C. for 3 hrs. The clear solution was stirred at room temperature for 24 hours. The precipitate was collected by filtration and washed with acetone. The N9,N2-diacetylated guanine (9) was dried and identified by 1H-NMR. [0101] M.P.=Decomp. 270 C. [0102] 1H-NMR (DMSO-d6): [0103] 12.1(bs, 1H-(N)), 8.53(s, 1H, H-(C8)); 2.91(s, 3H, Ac-(N9)); 2.31(s, 3H, -(N2-COCH3)). [0104] (5 g, 21.25 mmol) of (9) were suspended in 100 ml of dry pyridine and excess of diisopropyl ethylamine (DIEA). Then (5.91 g, 25.51 mmol) of diphenylcarbamoyl chloride ere added in portions. The reaction mixture turned orange immediately. Stirring continued for 2 hrs at r.t. then 20 nml if ice-cold water were added. The mixture was stirred for 10 minutes more and solvent was removed under reduced pressure. 100 ml of ethanol and 100 nml of water were added and the mixture was reflexed for 1.5 hr. After cooling to the room temperature, vigorous stirring continued for over night. The desired product (10) was collected by filtration and washed with 50 ml of ethanol, dried and characterized. [0105] M.P.=185 C. [0106] 1H-NMR (DMSO-d6): [0107] 10.7(s, 1H, H-(N2)); 8.55(s, 1H, H-(C8)); 7.61-7.38(m , 10H, aromatic); 2.28(s, 3H, -COCH3).

References: [1]European Journal of Organic Chemistry,2009,p. 1398 - 1406.
[2]Synthetic Communications,1999,vol. 29,p. 3003 - 3009.
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2003,vol. 42,p. 651 - 654.
[4]Bulletin of the Chemical Society of Ethiopia,2010,vol. 24,p. 425 - 432.
[5]Canadian Journal of Chemistry,1987,vol. 65,p. 1436 - 1437.
[6]Synthetic Communications,2001,vol. 31,p. 1399 - 1419.
[7]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 945 - 948.
Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 1109 - 1113.
[8]Angewandte Chemie - International Edition,2007,vol. 46,p. 7420 - 7424.
[9]Tetrahedron,2001,vol. 57,p. 4035 - 4038.
[10]Patent: US2004/34043,2004,A1 .Location in patent: Page/Page column 8-9.
[11]Organic Letters,2015,vol. 17,p. 4933 - 4935.

3
[ 98485-52-0 ]
[ 3056-33-5 ]
7-allyloxymethylguanine [ No CAS ]
9-allyloxymethylguanine [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 945 - 948.
Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 1109 - 1113.
[2]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 945 - 948.
Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 1109 - 1113.

4
[ 98485-52-0 ]
[ 3056-33-5 ]
7-allyloxymethyl-N-acetylguanine [ No CAS ]
9-allyloxymethyl-N-acetylguanine [ No CAS ]

5
[ 109-86-4 ]
[ 108-24-7 ]
[ 3056-33-5 ]
[ 75128-73-3 ]
[ 91702-60-2 ]

References: [1]Pharmaceutical Chemistry Journal,1985,vol. 19,p. 806 - 809.
Khimiko-Farmatsevticheskii Zhurnal,1985,vol. 19,p. 1371 - 1375.

6
[ 3511-19-1 ]
[ 3056-33-5 ]
[ 106445-17-4 ]

References: [1]Canadian Journal of Chemistry,1986,vol. 64,p. 1885 - 1889.

7
[ 3511-19-1 ]
[ 3056-33-5 ]
[ 106445-16-3 ]
[ 106445-15-2 ]

References: [1]Canadian Journal of Chemistry,1986,vol. 64,p. 1885 - 1889.

8
[ 84245-11-4 ]
[ 3056-33-5 ]
[ 84222-48-0 ]
[ 82410-30-8 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 759 - 761.
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 759 - 761.
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2003,vol. 42,p. 651 - 654.

9
[ 83-01-2 ]
[ 3056-33-5 ]
[ 112233-74-6 ]

Yield	Reaction Conditions	Operation in experiment
		[0100] A suspension of (5 g, 33 mmol) of guanine in 100 N-methy-2-pyrrolidinone NMP) and 20 ml acetic anhydride was heated to 150 C. for 3 hrs. The clear solution was stirred at room temperature for 24 hours. The precipitate was collected by filtration and washed with acetone. The N9,N2-diacetylated guanine (9) was dried and identified by 1H-NMR. [0101] M.P.=Decomp. 270 C. [0102] 1H-NMR (DMSO-d6): [0103] 12.1(bs, 1H-(N)), 8.53(s, 1H, H-(C8)); 2.91(s, 3H, Ac-(N9)); 2.31(s, 3H, -(N2-COCH3)). [0104] (5 g, 21.25 mmol) of (9) were suspended in 100 ml of dry pyridine and excess of diisopropyl ethylamine (DIEA). Then (5.91 g, 25.51 mmol) of diphenylcarbamoyl chloride ere added in portions. The reaction mixture turned orange immediately. Stirring continued for 2 hrs at r.t. then 20 nml if ice-cold water were added. The mixture was stirred for 10 minutes more and solvent was removed under reduced pressure. 100 ml of ethanol and 100 nml of water were added and the mixture was reflexed for 1.5 hr. After cooling to the room temperature, vigorous stirring continued for over night. The desired product (10) was collected by filtration and washed with 50 ml of ethanol, dried and characterized. [0105] M.P.=185 C. [0106] 1H-NMR (DMSO-d6): [0107] 10.7(s, 1H, H-(N2)); 8.55(s, 1H, H-(C8)); 7.61-7.38(m , 10H, aromatic); 2.28(s, 3H, -COCH3).

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 9207 - 9212.
[2]Tetrahedron,2001,vol. 57,p. 4035 - 4038.
[3]Canadian Journal of Chemistry,1987,vol. 65,p. 1436 - 1437.
[4]Patent: US2004/34043,2004,A1 .Location in patent: Page/Page column 8-10.

10
[ 102728-65-4 ]
[ 3056-33-5 ]
[ 75128-73-3 ]
[ 91702-60-2 ]

References: [1]Pharmaceutical Chemistry Journal,1985,vol. 19,p. 806 - 809.
Khimiko-Farmatsevticheskii Zhurnal,1985,vol. 19,p. 1371 - 1375.

11
[ 97151-26-3 ]
[ 3056-33-5 ]
[ 97151-29-6 ]
[ 97151-28-5 ]
[ 97151-27-4 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1242 - 1245.

12
[ 3056-33-5 ]
Acetic acid 2-benzyloxy-1-methyl-ethoxymethyl ester [ No CAS ]
N-[7-(2-Benzyloxy-1-methyl-ethoxymethyl)-6-oxo-6,7-dihydro-1H-purin-2-yl]-acetamide [ No CAS ]
[ 103025-02-1 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1384 - 1389.
[2]Journal of Medicinal Chemistry,1986,vol. 29,p. 1384 - 1389.

13
[ 3056-33-5 ]
Acetic acid 2-benzyloxy-1-fluoromethyl-ethoxymethyl ester [ No CAS ]
[ 103024-87-9 ]
[ 103024-86-8 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1384 - 1389.
[2]Journal of Medicinal Chemistry,1986,vol. 29,p. 1384 - 1389.

14
[ 3056-33-5 ]
Acetic acid 2-benzyloxy-1-chloromethyl-ethoxymethyl ester [ No CAS ]
[ 103025-03-2 ]
[ 103024-99-3 ]