Ethyl orthoformate → 5,7-Dichloropyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1023298Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([Cl:12])[CH:3]=1.[CH:13](OCC)(OCC)OCC>>[Cl:11][C:6]1[C:7]2[C:8](=[O:9])[NH:10][CH:13]=[N:1][C:2]=2[CH:3]=[C:4]([Cl:12])[N:5]=1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 580930524-Amino-2,6-dichloronicotinamide

Product 1

HCID 1357415885,7-Dichloropyrido[4,3-d]pyrimidin-4(3H)-one

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-Amino-2,6-dichloronicotinamide (2.06 g, 10.0 mmol) and triethyl orthoformate (20 mL) was heated at 150° C. in a ChemGlass pressure vessel (heavy wall, 150 mL) for 6 hours and evaporated under reduced pressure to afford the crude title compound. 1H NMR (DMSO-d6) δ 7.72 (s, 1H), 8.31 (1H); ESI-MS m/z 216.0 (MH+).

Workup

customevaporated under reduced pressure

Sources & evidence

ORD record: ord-5759089af93e4f76adfd2b41c1c3bef4
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722692B2

Reaction notes

Loading…