100061-59-4

Basic information

• Product Name: 2,6-DiaMino-4-(benzyloxy)pyriMidine
• Synonyms: 2,6-DiaMino-4-(benzyloxy)pyriMidine;NU 6038
• CAS NO: 100061-59-4
• Molecular Formula: C₁₁H₁₂N₄O
• Molecular Weight: 216.23918
• Product Categories: Heterocycles, Nucleotides, Bases & Related Reagents
• Mol File: 100061-59-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2,6-DiaMino-4-(benzyloxy)pyriMidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DiaMino-4-(benzyloxy)pyriMidine(100061-59-4)
• EPA Substance Registry System: 2,6-DiaMino-4-(benzyloxy)pyriMidine(100061-59-4)

Safety Data

• Hazardous Substances Data: 100061-59-4(Hazardous Substances Data)

Usage

Uses

2,6-Diamino-4-(benzyloxy)pyrimidine is a reactant used in the preparation of a series of 4(6)-(benzyloxy)-2,6(4)-diamino-5-(nitro or nitroso)pyrimidine derivatives as inhibitors of human O6-alkylguanine-DNA alkyltransferase (AGAT).

Upstream product

• 156-83-2 6-chloro-pyrimidine-2,4-diyldiamine 
• 100-51-6 benzyl alcohol 

Downstream Products

• 831-91-4 Benzyl phenyl sulfide 
• 56-06-4 2,6-diaminopyrimidin-4-ol 
• 101724-61-2 2,4-diamino-6-(benzyloxy)-5-nitrosopyrimidine 
• 1292801-98-9 tert-butyl 2-(3-(2-amino-6-(benzyloxy)-9H-purin-8-yl)propanamido)ethylcarbamate 
• 1292801-96-7 3-(2-amino-6-(benzyloxy)-9H-purin-8-yl)propanoic acid 
• 1292801-97-8 methyl 3-(2-amino-6-(benzyloxy)-9H-purin-8-yl)propanoate 
• 745822-41-7 8-[(3-O-acetyl-2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]-2',3',5,'-tri-O⁶-benzoyl-N²-(2-methylpropanoyl)guanosine 
• 745822-42-8 O⁶-benzyl-N²-(2-methylpropanoyl)-8-[(2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]guanosine 
• 745822-40-6 8-[(3-O-acetyl-2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]-O⁶-N²-(2-methylpropanoyl)guanine 
• 745822-38-2 2-(3-O-acetyl-2,4,6-tri-O-benzyl-α-D-mannopyranosyl)-N-[2-amino-6-(benzyloxy)-5-nitrosopyrimidin-4-yl]acetamide 
• 745822-39-3 8-[(3-O-acetyl-2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]-O⁶-benzylguanine 

Relevant articles and documents

NOVEL STING AGONISTS

The present invention provides compounds of Formula I′: wherein , W, X, Y, Z, Z1, Z2, R1, R2, R3, R4 and R5 are as defined herein, or a stereoisomer, tautomer, pharmaceutically acceptable salt, prodrug ester or solvate form thereof, wherein all of the variables are as defined herein. These compounds are effective at modulating the STING protein and thus can be used as medicaments for treating or preventing disorders affected by the agonism of STING.

Cyclin dependent kinase inhibitors

A range is disclosed of pyrimidine derivatives (I) which can act as inhibitors of cyclin dependent kinases (CDK's) and which thereby can provide useful therapeutic compounds for use in treatment of tumours or other cell proliferation disorders. The compounds of this invention bind to CDK molecules in a manner that appears to differ from that of known CDK inhibitors such as olomoucine and roscovitine. In formula (I), X is O, S or CHRxwhere Rxis H or C1-4alkyl; D is H or NZ1Z2where Z1and Z2are each independently H, C1-4alkyl, C1-4hydroxyalkyl, optionally substituted aryl or optionally substituted aralkyl; A is selected from H, C1-4alkyl, C1-4alkoxy, hydroxy, CH2(CH2)nOH (n=1-4), and NRa1Ra2where Ra1and Ra2are each independently H or C1-4alkyl; Y is or includes an optionally substituted 4- to 8-membered carbocyclic or heterocyclic ring; D′ is H or NZ3Z4where Z3and Z4are each independently H, C1-4alkyl, C1-4hydroxyalkyl, optionally substituted aryl or optionally-substituted aralkyl; E is selected from NO, NO2, N═N—Ar where Ar is an optionally substituted aryl or optionally substituted aralkyl, NRe1Re2or Nre1Nre2Re3(Re1, Re2and Re3each being independently H, C1-4alkyl, C1-4hydroxyalkyl, an optionally substituted aryl or an optionally substituted aralkyl), C(Re)═U (Rebeing hydrogen, C1-4alkyl or substituted alkyl, e.g. hydroxyalkyl, or an unsubstituted or substituted aryl or aralkyl, e.g. benzyl, and U being selected from O, Nre′, NORe′ and N—NRe′Re″ where Re′ and Re″ are each independently H, C1-4alkyl or CONH2), T, CH2T, CHT2and CT3, where T is a halide I, Br, Cl or F.

4-Alkoxy-2,6-diaminopyrimidine derivatives: inhibitors of cyclin dependent kinases 1 and 2.

The cyclin dependent kinase (cdk) inhibitor NU6027, 4-cyclohexylmethoxy-5-nitroso-pyrimidine-2,6-diamine (IC(50) vs cdk1/cyclinB1=2.9+/-0.1 microM and IC(50) vs cdk2/cyclinA3=2.2+/-0.6 microM), was used as the basis for the design of a series of 4-alkoxy-2,6-diamino-5-nitrosopyrimidine derivatives. The synthesis and evaluation of 21 compounds as potential inhibitors of cyclin-dependent kinases 1 and 2 is described and the structure-activity relationships relating to NU6027 have been probed. Simple alkoxy- or cycloalkoxy-groups at the O(4)-position were tolerated, with the 4-(2-methylbutoxy)-derivative (IC(50) vs cdk1/cyclinB1=12+/-2 microM and cdk2/cyclinA3=13+/-4 microM) retaining significant activity. Substitutions at the N(6) position were not tolerated. Replacement of the 5-nitroso substituent with ketone, oxime and semicarbazone groups essentially abolished activity. However, the derivative bearing an isosteric 5-formyl group, 2,6-diamino-4-cyclohexylmethoxy-pyrimidine-5-carbaldehyde, showed modest activity (IC(50) vs cdk1/cyclinB1=35+/-3 microM and cdk2/cyclinA3=43+/-3 microM). The X-ray crystal structure of the 5-formyl compound bound to cdk2 has been determined to 2.3A resolution. The intramolecular H-bond deduced from the structure with NU6027 bound to cdk2 is not evident in the structure with the corresponding formyl compound. Thus the parent compound, 4-cyclohexylmethoxy-5-nitrosopyrimidine-2,6-diamine (NU6027), remains the optimal basis for future structure-activity studies for cyclin-dependent kinase inhibitors in this series.