7H-Pyrrolo[2,3-d]pyrimidine-2,4-diol Chemical Properties

Melting point:

>250°C

Density 

1.516±0.06 g/cm3(Predicted)

storage temp. 

-20°C Freezer

solubility 

DMF, DMSO (Slightly)

form 

Solid

pka

11.22±0.20(Predicted)

color 

Brown to Black

InChI

InChI=1S/C6H5N3O2/c10-5-3-1-2-7-4(3)8-6(11)9-5/h1-2H,(H3,7,8,9,10,11)

InChIKey

HASUWNAFLUMMFI-UHFFFAOYSA-N

SMILES

C1(=O)NC(=O)C2C=CNC=2N1

Safety Information

Hazard Codes 

Xi

HS Code 

2933599590

7H-Pyrrolo[2,3-d]pyrimidine-2,4-diol Usage And Synthesis

Chemical Properties

Pink to Brown Solid

Uses

2,4-Dihydroxypyrrolo[2,3-d]pyrimidine (cas# 39929-79-8) is a compound useful in organic synthesis.

Synthesis

A suspension of 6-aminouracil (6.35 g, 50.0 mmol) and sodium acetate (4.10 g, 50.0 mmol) was formed in 50 mL of water. The reaction system was heated to 72 °C, followed by slow dropwise addition of 50% aqueous chloroacetaldehyde (11.8 g, 75.2 mmol). After the dropwise addition, the reaction temperature was raised to 80 °C and the reaction was continued with stirring for 60 min. Upon completion of the reaction, the mixture was cooled to room temperature and the resulting solid product was collected by filtration. The solid was washed sequentially with water and acetone and subsequently dried under vacuum to afford 2,4-dihydroxypyrrolo[2,3-d]pyrimidine (6.46 g, 86% yield) as a light brown solid. The structure of the product was confirmed by 1H-NMR (400 MHz, DMSO-d6) and mass spectrometry: 1H-NMR δ 11.45 (s, 1H), 11.10 (s, 1H), 10.48 (s, 1H), 6.64-6.51 (m, 1H), 6.22 (t, J = 2.5 Hz, 1H); MS (m/z) [M + H] + 152.06 .

References

[1] Tetrahedron, 2014, vol. 70, # 33, p. 4947 - 4956
[2] Patent: WO2018/137036, 2018, A1. Location in patent: Paragraph 00233; 00234
[3] Synlett, 2005, # 5, p. 744 - 750
[4] Patent: WO2009/37467, 2009, A1. Location in patent: Page/Page column 15-16; 13

7H-Pyrrolo[2,3-d]pyrimidine-2,4-diol(39929-79-8)Related Product Information

• Butylated Hydroxytoluene
• Chrysin
• Triclosan
• 1,3-Dihydroxyacetone
• 2-ISOPROPYL-6-METHYL-4-PYRIMIDINOL
• DEAZAPURINE
• 1-Hydroxyethylidene-1,1-diphosphonic acid
• 3-Diethylaminophenol
• 2-Chloro-7-cyclopentyl-N,N-dimethyl-H-pyrrolo[2,3-d]pyrimidine-6-carboxamide
• 4-Chloro-5,6-diMethyl-7H-pyrrolo[2,3-d]pyriMidine
• N-Methyl-N-((3S,4S)-4-Methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyriMidin-4-aMine
• Tofacitinib Impurity 29
• N-Hydroxysuccinimide
• CYANOACETIC ACID-OSU
• 1-Benzyl-4-methyl-piperidin-3-one hydrochloride
• 6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE
• Benzyl chloride
• 4-(Hydroxyamino)-4-oxobutanoic acid