6-Amino-5-(2,2-diethoxyethyl)-2-mercaptopyrimidin-4-OL

Base Information

• Chemical Name: 6-Amino-5-(2,2-diethoxyethyl)-2-mercaptopyrimidin-4-OL
• CAS No.: 7400-05-7
• Molecular Formula: C10H17N3O3S
• Molecular Weight: 259.329
• Hs Code.: 29335990
• NSC Number: 59249
• UNII: YVX56FS6AO
• DSSTox Substance ID: DTXSID70224791
• Mol file: 7400-05-7.mol

Synonyms:7400-05-7;6-AMINO-5-(2,2-DIETHOXYETHYL)-2-MERCAPTOPYRIMIDIN-4-OL;6-Amino-5(2,2-diethoxyethyl)-4-hydroxy-2-mercaptopyrimidine;NSC59249;YVX56FS6AO;6-amino-5-(2,2-diethoxyethyl)-2-sulfanylidene-1H-pyrimidin-4-one;6-Amino-5-(2,2-diethoxyethyl)-2-mercapto-4-pyrimidinol;NSC-59249;6-Amino-5-(2,2-diethoxyethyl)-2,3-dihydro-2-thioxo-4(1H)-pyrimidinone;6-Amino-5-(2,2-diethoxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one;NSC 59249;UNII-YVX56FS6AO;NCIOpen2_002353;SCHEMBL1002933;DTXSID70224791;6-Amino-5(2,2-diethoxyethyl)-4-hydroxy-2-mercaptopyrimidine ,97%;AB2613;MFCD02094192;AKOS022172964;DS-7168;SB60670;CS-0006821;FT-0661729;FT-0687944;A916483;J-518232;6-Amino-5-(2,2-diethoxy-ethyl)-2-mercapto-pyrimidin-4-ol;6-amino-5-(2,2-diethoxyethyl)-2-mercapto-pyrimidin-4-ol;6-amino-5-(2,2-diethoxyethyl)-2-sulfanyl-pyrimidin-4-ol;4(1H)-PYRIMIDINONE, 6-AMINO-5-(2,2-DIETHOXYETHYL)-2,3-DIHYDRO-2-THIOXO-;5-PYRIMIDINEACETALDEHYDE, 4-AMINO-6-HYDROXY-2-MERCAPTO-, DIETHYL ACETAL

Chemical Property of 6-Amino-5-(2,2-diethoxyethyl)-2-mercaptopyrimidin-4-OL

Chemical Property:

• Appearance/Colour: White crystalline solid
• Melting Point: > 300°C
• Refractive Index: 1.578
• PKA: 8.08±0.25(Predicted)
• PSA: 129.29000
• Density: 1.27 g/cm³
• LogP: 1.57590
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO, Methanol
• XLogP3: 0
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 259.09906259
• Heavy Atom Count: 17
• Complexity: 338

Purity/Quality:

98% ^*data from raw suppliers

6-Amino-5(2,2-diethoxyethyl)-4-hydroxy-2-mercaptopyrimidine ^*data from reagent suppliers

Safty Information:

• Statements: 22-40
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(CC1=C(NC(=S)NC1=O)N)OCC
• Uses: Intermediate in the production of thymidine phosphorylase inhibitors.

Technology Process of 6-Amino-5-(2,2-diethoxyethyl)-2-mercaptopyrimidin-4-OL

There total 5 articles about 6-Amino-5-(2,2-diethoxyethyl)-2-mercaptopyrimidin-4-OL 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: 64.0%

ethyl 2-cyano-4,4-diethoxybutyrate (52133-67-2) + thiourea (17356-08-0) → 6-amino-5-(2,2-diethoxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (7400-05-7)

Guidance literature:

With sodium ethanolate; In ethanol; N,N-dimethyl-formamide; for 6h; Heating;

Reference yield: 62.0%

ethyl 2-cyano-4,4-diethoxybutyrate (52133-67-2) + thiourea (17356-08-0) → 6-amino-5-(2,2-diethoxy)-2-mercaptopyrimidine-4-ol (7400-05-7)

Guidance literature:

With sodium ethanolate; In ethanol; Reflux;

Reference yield:

Bromoacetaldehyde diethyl acetal (2032-35-1) → 6-amino-5-(2,2-diethoxy)-2-mercaptopyrimidine-4-ol (7400-05-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaI, K₂CO₃

2: NaOEt / ethanol

With sodium ethanolate; potassium carbonate; sodium iodide; In ethanol;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<827::AID-EJOC827>3.0.CO;2-B

upstream raw materials:

ethyl 2-cyano-4,4-diethoxybutyrate

thiourea

Bromoacetaldehyde diethyl acetal

Downstream raw materials:

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

(S)-3-tert-Butoxycarbonylamino-4-(4-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-butyric acid benzyl ester

(R)-3-tert-Butoxycarbonylamino-4-(4-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-butyric acid benzyl ester

(S)-4-(4-Azido-pyrrolo[2,3-d]pyrimidin-7-yl)-3-tert-butoxycarbonylamino-butyric acid benzyl ester

Refernces

• 1、 -. "6-methyl 7-position-denitrified purine nucleoside compounds and application thereof". Paragraph 0091; 0096; 0097; 0098. . Retrieved 2017/09/02.
• 2、 Kim, Jiae,Wang, Ligong,Li, Yongfeng,Becnel, Kimberlynne D.,Frey, Kathleen M.,Garforth, Scott J.,Prasad, Vinayaka R.,Schinazi, Raymond F.,Liotta, Dennis C.,Anderson, Karen S.. "Pre-steady state kinetic analysis of cyclobutyl derivatives of 2′-deoxyadenosine 5′-triphosphate as inhibitors of HIV-1 reverse transcriptase". supporting information; experimental part. p. 4064 - 4067. Retrieved 2012/07/14.