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| | 7H-Pyrrolo[2,3-d]pyrimidine-2,4-diol Basic information |
| Product Name: | 7H-Pyrrolo[2,3-d]pyrimidine-2,4-diol | | Synonyms: | 4-hydroxy-1,5-dihydropyrrolo[3,2-d]pyrimidin-6-one;Tofacitinib Impurity 188;1,7-dihydro-2H-pyrrolo[2,3-d]pyrimidine-2,4(3H)-dione;1H-PYRROLO-[2,3-D]-PYRIMIDINE-2,4(3H,7H)-DIONE;1,7-DIHYDRO-PYRROLO[2,3-D]PYRIMIDINE-2,4-DIONE;2,4-Dihydroxy-1H-pyrrolo[2,3-d]pyrimidine;2,4-Dihydroxy-7-deazapurine;7H-Pyrrolo[2,3-d]pyrimidine-2,4-diol | | CAS: | 39929-79-8 | | MF: | C6H5N3O2 | | MW: | 151.12 | | EINECS: | | | Product Categories: | Heterocycle-Pyrimidine series;Nucleotides and Nucleosides;Bases & Related Reagents;Intermediates;Nucleotides;Fused Ring Systems | | Mol File: | 39929-79-8.mol | ![7H-Pyrrolo[2,3-d]pyrimidine-2,4-diol Structure](CAS/GIF/39929-79-8.gif) |
| | 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 |
| 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 Preparation Products And Raw materials |
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