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

Safety Information

HazardClass 

IRRITANT

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(519032-08-7)Related Product Information

• 5-Methyl-1,3,4-oxadiazole-2-carboxylic acid potassium salt
• BENZYL [1-[4-[[(4-FLUOROBENZYL)AMINO]CARBONYL]-5-HYDROXY-1-METHYL-6-OXO-1,6-DIHYDROPYRIMIDIN-2-YL]-1-METHYLETHYL]CARBAMATE
• 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-1-METHYL-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER
• 4-Pyrimidinecarboxylic acid, 1,6-dihydro-2-methyl-6-oxo-
• 6-Oxo-3H-pyrimidine-4-carboxylic acid
• 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER