170170-13-5

Basic information

• Product Name: 5-METHYL-7H-PYRROLO[2,3-D]PYRIMIDINE-2,4-DIAMINE
• Synonyms: 5-METHYL-7H-PYRROLO[2,3-D]PYRIMIDINE-2,4-DIAMINE;5-methyl-1H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
• CAS NO: 170170-13-5
• Molecular Formula: C₇H₉N₅
• Molecular Weight: 163.17986
• Mol File: 170170-13-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 357.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.71±0.1 g/cm3(Predicted)
• PKA: 12.96±0.20(Predicted)
• CAS DataBase Reference: 5-METHYL-7H-PYRROLO[2,3-D]PYRIMIDINE-2,4-DIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-7H-PYRROLO[2,3-D]PYRIMIDINE-2,4-DIAMINE(170170-13-5)
• EPA Substance Registry System: 5-METHYL-7H-PYRROLO[2,3-D]PYRIMIDINE-2,4-DIAMINE(170170-13-5)

Safety Data

• Hazardous Substances Data: 170170-13-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 6684, 1995 DOI: 10.1021/jo00126a017

Upstream product

• 5117-87-3 2-amino-4-methyl-3-furonitrile 
• 50-01-1 guanidine hydrochloride 
• 116-09-6 hydroxy-2-propanone 
• 109-77-3 malononitrile 

Downstream Products

• 1221521-89-6 2,4-diamino-5-methyl-6-(2',4',5'-trichlorophenylthio)pyrrolo[2,3-d]pyrimidine 
• 1221521-88-5 2,4-diamino-5-methyl-6-(3',5'-dimethylphenylthio)pyrrolo[2,3-d]pyrimidine 
• 1221521-91-0 2,4-diamino-5-methyl-6-(3',4',5'-trimethoxyphenylthio)pyrrolo[2,3-d]pyrimidine 
• 1221521-87-4 2,4-diamino-5-methyl-6-(2',6'-dimethylphenylthio)pyrrolo[2,3-d]pyrimidine 
• 870754-13-5 diethyl N-[4-[(2,4-diamino-5-methyl-3,4-dihydro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl]-L-glutamate 

Relevant articles and documents

Targeting species specific amino acid residues: Design, synthesis and biological evaluation of 6-substituted pyrrolo[2,3-d]pyrimidines as dihydrofolate reductase inhibitors and potential anti-opportunistic infection agents

To combine the potency of trimetrexate (TMQ) or piritrexim (PTX) with the species selectivity of trimethoprim (TMP), target based design was carried out with the X-ray crystal structure of human dihydrofolate reductase (hDHFR) and the homology model of Pneumocystis jirovecii DHFR (pjDHFR). Using variation of amino acids such as Met33/Phe31 (in pjDHFR/hDHFR) that affect the binding of inhibitors due to their distinct positive or negative steric effect at the active binding site of the inhibitor, we designed a series of substituted-pyrrolo[2,3-d]pyrimidines. The best analogs displayed better potency (IC50) than PTX and high selectivity for pjDHFR versus hDHFR, with 4 exhibiting a selectivity for pjDHFR of 24-fold.

Analogues of 4-[(7-Bromo-2-methyl-4-oxo-3 H -quinazolin-6-yl)methylprop-2- ynylamino]- N -(3-pyridylmethyl)benzamide (CB-30865) as potent inhibitors of nicotinamide phosphoribosyltransferase (Nampt)

We have shown previously that the target of the potent cytotoxic agent 4-[(7-bromo-2-methyl-4-oxo-3H-quinazolin-6-yl)methyl-prop-2-ynylamino] -N-(3-pyridylmethyl)benzamide (CB38065, 1) is nicotinamide phosphoribosyltransferase (Nampt). With its cellular target known we sought to optimize the biochemical and cellular Nampt activity of 1 as well as its cytotoxicity. It was found that a 3-pyridylmethylamide substituent in the A region was critical to cellular Nampt activity and cytotoxicity, although other aromatic substitution did yield compounds with submicromolar enzymatic inhibition. Small unsaturated groups worked best in the D-region of the molecule, with 3,3-dimethylallyl providing optimal potency. The E region required a quinazolin-4-one or 1,2,3-benzotriazin-4-one group for activity, and many substituents were tolerated at C2 of the quinazolin-4-one. The best compounds showed subnanomolar inhibition of Nampt and low nanomolar cytotoxicity in cellular assays.

A one-step ring transformation/ring annulation approach to pyrrolo[2,3-d]pyrimidines. A new synthesis of the potent DHFR inhibitor TNP-351

Condensation of amidines with 2-amino-3-cyanofurans gives 2-substituted-4-aminopyrrolo[2,3-d]pyrimidines by a ring-opening, ring-recyclization sequence of reactions through which the starting furan 2-amino nitrogen becomes the pyrrole nitrogen of the final product and one of the amidine nitrogens becomes N-1 of the fused pyrimidine ring. 2,4-Diamino-5-[2-(4-carbethoxyphenyl)ethyl]pyrrolo[2,3-d]pyrimidine, a key intermediate in the synthesis of the DHFR inhibitor TNP-351, has been prepared in one step by reaction of ethyl 4-[2-(2-amino-3-cyanofuran-4-yl)ethyl]benzoate with guanidine.