5-Methylisocytosine

Base Information

• Chemical Name: 5-Methylisocytosine
• CAS No.: 15981-91-6
• Molecular Formula: C5H7N3O
• Molecular Weight: 125.13
• European Community (EC) Number: 863-203-0
• NSC Number: 60208
• UNII: 9OC5QA5FKI
• DSSTox Substance ID: DTXSID60166732
• Nikkaji Number: J82.471B
• Wikidata: Q83035970
• Mol file: 15981-91-6.mol

Synonyms:15981-91-6;2-amino-5-methylpyrimidin-4(3h)-one;5-Methylisocytosine;2-Amino-5-methylpyrimidin-4-ol;2-amino-5-methyl-1H-pyrimidin-6-one;4(1H)-Pyrimidinone, 2-amino-5-methyl-;2-Amino-5-methyl-4-pyrimidinol;9OC5QA5FKI;NSC 60208;NSC-60208;2-Amino-5-methyl-4(3H)-pyrimidinone;4(1H)-Pyrimidinone, 2-amino-5-methyl- (7CI,8CI,9CI);4(1H)-Pyrimidinone, 2-amino-5-methyl- (8CI)(9CI);2-amino-5-methylpyrimidin-4-one;NSC60208;UNII-9OC5QA5FKI;EC-000.2047;SCHEMBL162683;SCHEMBL10119987;DTXSID60166732;2-Amino-5-methyl-pyrimidin-4-ol;amino-4-hydroxy-5-methylpyrimidine;BCP30400;MFCD09754456;STL301845;AKOS006375342;AKOS016363826;SB57595;2-Amino-5-methyl-4(3H)-pyrimidinone #;CS-16309;2-Amino-5-methyl-4-pyrimidinol, AldrichCPR;CS-0095202;FT-0709233;2-amino-5-methyl-3,4-dihydropyrimidin-4-one;2-Amino-5-methyl-4-oxo-3,4-dihydropyrimidine;F19190;EN300-2945657;A900948;Z3235158428;5-Methylisocytosine pound>>2-Amino-5-methylpyrimidin-4-ol

Chemical Property of 5-Methylisocytosine

Chemical Property:

• Melting Point: 277-279 °C
• Refractive Index: 1.651
• PKA: 9.74±0.50(Predicted)
• PSA: 71.77000
• Density: 1.44 g/cm³
• LogP: 0.24170
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 125.058911855
• Heavy Atom Count: 9
• Complexity: 204

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Amino-5-methyl-pyrimidin-4-ol ^*data from reagent suppliers

Safty Information:

• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(NC1=O)N

Technology Process of 5-Methylisocytosine

There total 12 articles about 5-Methylisocytosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

1,3-dimethylthymine (4401-71-2) + guanidine nitrate (113-00-8) → 2-amino-5-methylpyrimidin-4-one (15981-91-6)

Guidance literature:

at 80 - 90 ℃;

Reference yield: 76.0%

ethyl 2-formylpropionate (27772-62-9) + guanidine hydrochloride (50-01-1) → 2-amino-5-methylpyrimidin-4-one (15981-91-6) + 6-ethyl-5-methylisocytosine (134277-54-6) + 3,7-dimethyl-1H-pyrimido<1,2-a>pyrimidine-2,8-dione (134277-56-8) + 3,7-dimethyl-1H-pyrimido<1,2-a>pyrimidine-2,6-dione (134277-55-7)

Guidance literature:

In methanol; N,N-dimethyl-formamide; for 2h; Yields of byproduct given; Heating;

DOI:10.1002/jhet.5570280205

Reference yield: 58.4%

Methyl formate (107-31-3) + guanidine hydrochloride (50-01-1) + Ethyl propionate (105-37-3,20741-13-3) → 2-amino-5-methylpyrimidin-4-one (15981-91-6)

Guidance literature:

Methyl formate; Ethyl propionate; With sodium methylate; In N,N-dimethyl-formamide; at 20 ℃;

guanidine hydrochloride; In methanol; N,N-dimethyl-formamide; for 12h; Reflux;

upstream raw materials:

3-methylmalic acid

guanidine hydrochloride

1,3-dimethylthymine

guanidine nitrate

Downstream raw materials:

thymin

N²-benzoyl-5-methylisocytosine

N²-benzoyl-1-(3-O-benzoyl-4-O-[bis(4-methoxyphenyl)phenylmethyl]-β-D-ribopyranosyl)-5-methylisocytosine

Fmoc-PNA-iC(Boc)-OBn

Refernces

• 1、 Stoss,Kaes,Eibel,Thewalt. "Novel pyrimidine and pyrimidol[1,2-α]pyrimidine derivatives. By-products of a guanidine based thymine synthesis". . p. 231 - 236. Retrieved 1991.
• 2、 Seela, Frank,He, Yang,Wei, Changfu. "Parallel-stranded oligonucleotide duplexes containing 5- methylisocytosine-guanine and isoguanine-cytosine base pairs". . p. 9481 - 9500. Retrieved 2007/10/03.