2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine

Base Information

• Chemical Name: 2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine
• CAS No.: 7355-55-7
• Molecular Formula: C6H6 N4 O
• Molecular Weight: 150.14
• Hs Code.: 2933990090
• Mol file: 7355-55-7.mol

Synonyms:4H-Pyrrolo[2,3-d]pyrimidin-4-one,2-amino-1,7-dihydro- (9CI); 7H-Pyrrolo[2,3-d]pyrimidin-4-ol, 2-amino- (6CI);2-Amino-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one;2-Amino-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine;2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine;2-Amino-7H-pyrrolo[2,3-d]pyrimidin-4-ol; 7-Deazaguanine; NSC 62498

Chemical Property of 2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine

Chemical Property:

• Vapor Pressure: 2.2E-08mmHg at 25°C
• Melting Point: >230oC (dec.)
• Boiling Point: 452.7oC at 760 mmHg
• PKA: 10.83±0.20(Predicted)
• Flash Point: 227.6oC
• PSA: 87.56000
• Density: 1.87g/cm3
• LogP: 0.41460
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in N,N-Dimethylformamide, Dimethyl sulfoxide.

Purity/Quality:

97% ^*data from raw suppliers

7-Deazaguanine ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-37-60

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine (also known as 7-deazaguanine) is a key intermediate in the synthesis of nucleoside analogs, which are valuable for DNA studies, fluorescence labeling, sequencing, and nanotechnology applications. 2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine serves as a core structure for developing modified nucleosides with enhanced stability and functionality, as demonstrated by its use in a Boc protection strategy to efficiently synthesize 5-substituted 7-deazaguanine nucleosides without requiring prior chlorination. This approach enables mild deprotection conditions, making it suitable for sensitive derivatives.

Technology Process of 2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine

There total 1 articles about 2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine 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: 89.0%

2,6-diamino-4-pyrimidinone (626-46-0) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (7355-55-7)

Guidance literature:

Bromoacetaldehyde diethyl acetal; With hydrogenchloride; In water; at 90 ℃; for 0.666667h;

2,6-diamino-4-pyrimidinone; With sodium acetate; In water; at 80 ℃; for 2h;

DOI:10.1002/anie.202002295

Reference yield: 81.0%

2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (7355-55-7) → 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7)

Guidance literature:

With N,N-dimethyl-aniline; trichlorophosphate; for 2h; reflux;

Reference yield: 67.0%

benzoyl chloride (98-88-4) + 2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (7355-55-7) → N-(4-Oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-benzamide (88523-00-6)

Guidance literature:

With pyridine; at 85 ℃; for 0.5h;

upstream raw materials:

2,6-diamino-4-pyrimidinone

Bromoacetaldehyde diethyl acetal

Downstream raw materials:

N-(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide

N-(4-Oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-benzamide

2-acetamido-3,7-dihydropyrrolo<2,3-d>pyrimidin-4-one

2-Amino-6-[(dibenzylamino)-methyl]-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one

Refernces

A facile synthetic approach to 7-deazaguanine nucleosides via a boc protection strategy

10.1021/ol9007537

The research describes a facile synthetic approach to 7-deazaguanine nucleosides, which are compounds that can be used for structural and stability studies of DNA, DNA fluorescence labeling, sequencing, and the production of DNA-based nanoarrays. The study aimed to overcome the challenges in synthesizing 5-substituted 2-amino-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one nucleosides by developing an efficient route that avoids the need for converting the nucleoside core into a 4-chloro derivative prior to sugar coupling. The researchers utilized ω-substituted aldehydes, 2,6-diaminopyrimidin-4(3H)-one, Boc2O (tert-butyloxycarbonyl anhydride), and 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-R-D-erythro-pentofuranose in their synthesis process. The conclusions of the study highlight the successful development of a convenient, efficient, and general route to 5-substituted 2-amino-7-((2R,4R,5R)-tetrahydro-4-hydroxy-5-(hydroxymethyl)furan-2-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-ones, which includes the formation of key O4-t-Bu ether intermediates and demonstrates the potential for preparing guanine nucleosides. The Boc protection strategy proved to be efficient for the preparation of these nucleosides with sensitive functionalities, as the Boc and O4-t-butyl groups could be effectively removed under mild conditions.