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| | 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER Basic information |
| Product Name: | 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER | | Synonyms: | InterMediate E of Raltegravir;2-(2-(BenzyloxycarbonylaMino)propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyriMidine-4-Methyl forMate;Methyl 2-[1-[[(benzyloxy)carbonyl]aMino]-1-Methylethyl]-5,6-dihydroxypyriMidine-4-carboxylate;Methyl2-(1-{[(benzyloxy)carbonyl]aMino}-1-Methylethyl)-5,6-dihydroxypyriMidine-4-carboxyllate;Methyl 2-(2-(benzyloxycarbonyl)propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyriMidine-4-carboxylate;Methyl-2-(2-{[(benzyloxy)carbo;Methyl 2-(2-(benzyloxycarbonylamino)propan-2-yl)-5-hydroxy-6-oxo-l,6-dihydropyrimidine-4-carboxylate(Raltegravir);4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER | | CAS: | 519032-08-7 | | MF: | C17H19N3O6 | | MW: | 361.35 | | EINECS: | 917-658-8 | | Product Categories: | Heterocycle-Pyrimidine series;Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;519032-08-7 | | Mol File: | 519032-08-7.mol | ![4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER Structure](CAS/GIF/519032-08-7.gif) |
| | 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER Chemical Properties |
| Melting point | 186.3-187.0 °C | | density | 1.34±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | 4.50±1.00(Predicted) | | form | Solid | | color | White to Off-White | | InChI | InChI=1S/C17H19N3O6/c1-17(2,20-16(24)26-9-10-7-5-4-6-8-10)15-18-11(14(23)25-3)12(21)13(22)19-15/h4-8,21H,9H2,1-3H3,(H,20,24)(H,18,19,22) | | InChIKey | NIVUTAZNLHLBAN-UHFFFAOYSA-N | | SMILES | C1(C(C)(NC(OCC2=CC=CC=C2)=O)C)NC(=O)C(O)=C(C(OC)=O)N=1 |
| | 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER Usage And Synthesis |
| Chemical Properties | Brown Solid | | Uses | An intermediate in the preparation of HIV-integrase inhibitors | | Synthesis | The general procedure for the synthesis of methyl 2-(2-(benzyloxycarbonylamino)propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate from benzyl [2-amino-2-(oximido)-1,1-dimethylethyl]carbamate and dimethyl ethynedicarboxylate was as follows: benzyl 2-amino-2-(hydroxyimino)-1,1-dimethylethyl carbamate ( 2.0 g, 8.0 mmol) was dissolved in 30 mL of methanol and dimethyl acetylenedicarboxylate (DMAD, 1.1 mL, 9.0 mmol) was added slowly. The reaction mixture was stirred at room temperature for 2 h. Subsequently, a white oil was obtained by concentration under reduced pressure. This oily substance was mixed with 80 mL of xylene and stirred at 90 °C for 2 hours, then warmed up to 120 °C for 2 hours and finally refluxed under nitrogen protection for 12 hours. After completion of the reaction, the mixture was concentrated to give the crude product. The crude product was purified by recrystallization with 2 mL of methanol and 10 mL of tert-butyl methyl ether to afford the target compound 5 as a yellow solid (1.7 g, 58% yield). Its 1H-NMR (DMSO-d6) data were as follows: δ 7.35 (m, 5H), 5.00 (s, 2H), 3.83 (s, 3H), 1.48 (s, 6H); ESI-MS m/z 360 (M-), 384 (M + Na+). | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7114 - 7118 |
| | 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER Preparation Products And Raw materials |
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