6-Amino-1,5-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Base Information

• Chemical Name: 6-Amino-1,5-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• CAS No.: 63959-47-7
• Molecular Formula: C6H9N3O2
• Molecular Weight: 155.15500
• European Community (EC) Number: 821-282-9
• DSSTox Substance ID: DTXSID10407809
• Wikidata: Q82213150
• Mol file: 63959-47-7.mol

Synonyms:63959-47-7;6-amino-1,5-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione;6-amino-1,5-dimethylpyrimidine-2,4(1H,3H)-dione;6-amino-1,5-dimethylpyrimidine-2,4-dione;ZINC02576756;SCHEMBL15667389;DTXSID10407809;AKOS006279652;AT19385;CS-0135448;EN300-250707;Z1198159420

Chemical Property of 6-Amino-1,5-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Chemical Property:

• Melting Point: 327 °C (decomp)(Solv: water (7732-18-5))
• PSA: 81.14000
• Density: 1.257±0.06 g/cm3(Predicted)
• LogP: -0.04230
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 155.069476538
• Heavy Atom Count: 11
• Complexity: 257

Purity/Quality:

97% ^*data from raw suppliers

6-Amino-1,5-dimethylpyrimidine-2,4(1H,3H)-dione 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N(C(=O)NC1=O)C)N

Technology Process of 6-Amino-1,5-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

There total 2 articles about 6-Amino-1,5-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione 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:

ethyl 2-cyanopropionate (1572-99-2) + N-Methylurea (598-50-5) → 6-amino-1,5-dimethylpyrimidine-2,4-(1H,3H)-dione (63959-47-7)

Guidance literature:

With sodium methylate; In methanol; for 18h; Inert atmosphere; Reflux;

DOI:10.1021/acsmedchemlett.9b00050

Reference yield:

2-cyanopropanoic acid (632-07-5) + N-acetyl-N'-methylurea (623-59-6) → 6-amino-1,5-dimethylpyrimidine-2,4-(1H,3H)-dione (63959-47-7)

Guidance literature:

Reference yield:

6-amino-1,5-dimethylpyrimidine-2,4-(1H,3H)-dione (63959-47-7) → 6-(4-(furo[3,2-c]pyridin-4-yloxy)-2-methylphenyl)-1,5-dimethylpyrimidine-2,4(1H,3H)-dione

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium nitrite; copper(ll) bromide / acetonitrile; water / 48 h / 0 - 20 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 18 h / Inert atmosphere; Heating

3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere

4.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 12 h / 60 °C

5.1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 120 °C / Inert atmosphere

6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

6.2: 12 h / 20 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 10 wt% Pd(OH)2 on carbon; hydrogen; potassium carbonate; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; copper(ll) bromide; sodium nitrite; In 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 3.1: |Suzuki Coupling;

DOI:10.1021/acsmedchemlett.9b00050

upstream raw materials:

2-cyanopropanoic acid

N-acetyl-N'-methylurea

ethyl 2-cyanopropionate

N-Methylurea

Downstream raw materials:

6-amino-1,3,5-trimethyluracil

6-bromo-1,5-dimethylpyrimidine-2,4(1H,3H)-dione