4-chloro-5,8-dihydro-6H-pyrido[3,4-d]pyriMidine-7-carboxylic acid tert-butyl ester Chemical Properties

Boiling point:

395.8±42.0 °C(Predicted)

Density 

1.266±0.06 g/cm3(Predicted)

storage temp. 

-20°C, sealed storage, away from moisture

pka

-0.04±0.20(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C12H16ClN3O2/c1-12(2,3)18-11(17)16-5-4-8-9(6-16)14-7-15-10(8)13/h7H,4-6H2,1-3H3

InChIKey

XYHXUYOSXZHUSZ-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=C2CCN(C(OC(C)(C)C)=O)CC2=N1

4-chloro-5,8-dihydro-6H-pyrido[3,4-d]pyriMidine-7-carboxylic acid tert-butyl ester Usage And Synthesis

Synthesis

General procedure for the synthesis of tert-butyl 4-chloro-5,8-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate from tert-butyl 4-hydroxy-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate: to a solution of intermediate 1 (1.26 g, 5.02 mmol) in ethylene dichloride (DCE, 36 mL), sequentially added triphenylphosphine (PPh3, 2.69 g, 10.05 mmol) and carbon tetrachloride (CCl4, 1.46 mL, 15.07 mmol). The reaction mixture was heated to 70 °C and maintained for 2.5 hours. After completion of the reaction, the mixture was concentrated under reduced pressure and purified by silica gel (SiO2) column chromatography with ethyl acetate/hexane as eluent to afford the target compound as a light yellow solid (1.20 g, 88% yield). The mass spectrometry (ESI) calculated value of C12H16ClN3O2 was 269.09, and the measured value m/z 270.1 [M + H]+.1H NMR (400 MHz, CDCl3) δ: 8.79 (s, 1H), 4.65 (br s, 2H), 3.80-3.68 (m, 2H), 2.93-2.82 (m, 2H), 1.49 ( s, 9H).

References

[1] Patent: US2014/275120, 2014, A1. Location in patent: Paragraph 0160; 0161
[2] Patent: WO2011/29842, 2011, A1. Location in patent: Page/Page column 40-41
[3] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[4] Patent: US2016/75708, 2016, A1. Location in patent: Paragraph 0086; 0092
[5] Patent: KR2015/139962, 2015, A. Location in patent: Paragraph 0118-0119; 0131-0132

4-chloro-5,8-dihydro-6H-pyrido[3,4-d]pyriMidine-7-carboxylic acid tert-butyl ester(1053656-57-7)Related Product Information

• TERT-BUTYL 4-CHLORO-7,8-DIHYDROPYRIDO[4,3-D]PYRIMIDINE-6(5H)-CARBOXYLATE